Story Code: Mf, First, Voy, Exhib, Mast, Oral, Virgin, Sex

Hamish the caretaker was an interesting character. Nobody knew his age but he was a cuddly, round, bear-like man around 5’10" with white hair, white beard and a jovial, cheeky character. He wore the same loose shorts all year round. Come sun, rain or snow his strong hairy legs were always naked from his shorts down to his leather boots. He spent most of his time in the girl's wing where his office was. And whatever he was doing he always had time to stop and talk with girls walking past. Leaning on his broom, he would ask them how they were. He would ask about their teachers, their classwork, whether they were missing their family and what was on their minds.

Girls tended to confide in him since he was the only man in the school offering that kind of support. And it was heartfelt, he genuinely who cared about the students.

He was also very flirtatious and had a number of well-rehearsed lines. He would often tell girls in his soft Scottish accent that when he was younger he attended the school himself, "but in my day boys and girls were taught together, not separated." Then, when he had their attention, he would add, "we were in and out of each other’s dormitories all the time. As soon as the lights were out we were at it like rabbits." Then, looking at any nearby girl, "If only there had been a girl like you when I was here, I would I’ve been in your dormitory every night." This would frequently result in a deep red blush.

If a girl ever mentioned his white hair, he would trot out the old line, "Just because there’s snow on the roof doesn’t mean there isn’t a fire in the hearth," and he would gesture towards his head and his groin to make sure girls of all ages knew what he meant. If any girl said he looked like Father Christmas, he would say, "I am that other Father Christmas. I only come to tuck you up in bed if you’re feeling naughty." And if any girl ever said she was missing boys, he would say with a wink, "well I’m always here for you." He said all these things with a wicked twinkle in his eye and he would use the same lines for all girls whether sixth year or first year.

He was also very affectionate, stroking their arms, putting his arm around them and always offering hugs. But his hugs came with a warning, "You can have a hug any time, but I do suffer from WHD. That’s wandering hand disease." Any girl who came in for a hug he would warmly embrace, putting his huge arms around them like a warm, cuddly bear. But then his hands would drop down to their buttocks and give them a friendly squeeze. And sometimes he would press their buttocks in towards him and often as not, they would feel his large erection in his loose shorts. This would usually result in an exclamation, "Oh, Hamish!", Or just "Oh!".

His response was always, "with beautiful girls like you around I can’t stop that happening." Beyond that, he was never pushy, but if a girl expressed an interest in going further, he would always accommodate them.

One such girl was Sheila, just turned 13. Sheila was almost as tall as Hamish with shoulder length brown hair but, in complete contrast to him, as thin as a rake. She was confident around adults having been an only child raised by her parents and grandparents. Hamish reminded her of her grandad who was also cuddly with white whiskers, but he had passed away three years ago. Although her grandad had never been sexual with her, Hamish’s flirting seemed completely natural and made her feel grown up.

She was with a group of girls talking to Hamish in his office about being away from home, missing their parents. As they talked the other girls wandered off until she and Hamish were alone. She was looking a little lonely. He put his arm around her shoulder, and she came towards him for a hug. He engulfed her with his huge arms, hugging her warmly. And then he dropped his hands to her buttocks giving them a squeeze. She giggled.

He squeezed them again, pressing himself against her. "Oh, my," she said, with open eyes as she realised what was pressing against her stomach. He looked her in the eye and gave her a wink.

"I didn’t realise you…." She didn’t finish the sentence. He could see her mind ticking over. He squeezed her buttocks again. He could see her coming to a realisation with a slight smirk on her face, as she reached her right hand down between them to feel his shorts. She placed her hand on his erection. "Is that what I think it is?"

"It certainly is young lady. And with a beautiful lady like you in my arms, he was always going to rise up." She gave it a squeeze.

"I think I know what this is, but… I’ve never… I’ve never actually seen one."

"Well that’s not right," he said, "when I was at school we used to play a game, ‘I’ll show you if you show me’."

Her eyes widened as she considered this. After a pause, she asked, "what would you want me to show you?"

In response Hamish looked down at her chest. Then he looked her in the eye questioningly.

She looked a little embarrassed. "I haven’t actually got very much to show you there" she said.

"That’s no problem," he replied with a twinkle in his eye, "I’ve always preferred peaches to melons."

Sheila thought about this again. On the one hand, she really wanted to see her first cock and despite his age, she liked the fact that he felt completely safe and friendly. And on the other hand, well, the more she thought about it, she really wanted to show him her tits. She liked that he seemed interested in her small breasts and the prospect of seeing the excitement in his eyes when she showed him. This was becoming a very easy decision to make. "Okay," she said. "Who goes first?"

"Well," he replied, "I’ve done this before, so I’m quite happy to go first." He took a step back from her and lifted his shirt up to his belly, "I think you should do the honours." Tentatively, she reached down. "First, you need to untie the rope and then it’s just elastic you can pull them down. I’m not wearing any underwear so be prepared."

She fumbled with the loose knot in the rope until it was freed, then put her fingers inside the waistband either side of his hips and pulled down. After a few inches, the shorts would go no further, hampered by his cock. "You need to pull it out from the front to get round the obvious obstacle," he suggested.

She did as he said, pulling the waistband forward and then down and as she did so the top of his cock appeared. Stunned for a moment, she let go and looked at the top half of his cock and swollen purple head sticking out above his waistband. Her first sight off a male penis. "Keep going if you really want to see," he said. So she pulled them right down to his thighs and he let them drop to his feet, stepping of them.

She took another step back to get a good view. She had heard girls in the dormitory talking about boys with stiff willies, but she had never expected it to be so big. She suddenly felt very innocent and inexperienced. "I, I don’t know what to do with it," she stammered. "Do you think you could teach me?"

"I would be honoured to teach you what to do young lady, so you know how to please boys in the future. There are two main things you need to learn and that is how to use your hands and how to use your mouth." She was a little taken aback. She had heard girls in the dormitory talking about wanking boys off, which she knew involved hands. But her mouth? She wasn’t sure what that meant. Kissing? Now she was about to find out.

"First of all I’ll show you. The bit at the top, this swollen bit, is the most sensitive. And this part, this is the foreskin and you’ll see how, if I put my hand around it, it moves up and down." She was fascinated as she got to concentrate her gaze on his erection, watching his hand move up and down, covering and revealing the purple head. Watching was definitely making her tingly between her legs.

"Now you put your hand around it and see how it feels." She reached out and put her fingers around his erection, feeling how rigid and hard it felt, but how soft and warm the skin was on the outside. He put his hand over hers and showed her how to slowly stroke it up and down. "This is a really good skill to learn. If you can do this, you can keep any boy happy."

He took his hand away and left hers stroking him slowly up-and-down in full strokes. "Mmm that’s lovely. You have a natural touch. Delicious! Now you need to gradually speed up but you need to look in his eyes, and sense when is the right time to go faster."

She sped up but after a minute he stopped her. "If you carry on I’m going to shoot my load all over your lovely blouse." She wasn’t really sure what he was saying but kept silent.

"Now let’s see how you get on with your mouth. Kneel down, so your mouth is at the right level. That’s it. Now open your mouth. Make sure your teeth are well out of the way. And put it into your mouth. You can keep your hand around the shaft like you were just doing while you suck and lick the head with your lips and tongue as it’s going in and out."

She did as he asked, finding it strange to have it in her mouth, but at the same time, exciting and very sexy to be so close to his cock. A few minutes ago, she’d never even seen one. The whole experience was making her very wet.

As he moaned and was clearly enjoying having his cock in her mouth, she experienced a sense of sexual power that was exhilarating. She had been masturbating for a year or so, with vague thoughts in her head about naked men and stiff willies, but the reality was so much more exciting.

He was very close to coming, and while he would dearly have loved to unload into her mouth, he wanted to wait and anyway he hadn’t seen her tits yet. They’d hardly started. He pulled her to her feet. "That’s enough of that lesson for now, I’m sure we can continue another time. Anyway, it’s your turn I think," he said as he looked at her chest with another glint in his eye.

She knew what she had to do next and facing him directly, put her hands to her blouse. He watched as she unfastened the first three buttons, but then she stopped. "I feel shy," she said.

"It’s okay, you can turn your back to me if that helps. Or you can stop at any time, there’s no pressure." She turned away from him and he watched as she removed her blouse and then her bra. He loved the view of her long, slender, naked back. Then placing both her arms across her breasts, she turned back to him with a shy smile.

To match her toplessness he removed his shirt over his head and kicked off his boots. Now totally naked he moved forward and hugged her again, his bear like arms around her back, this time skin to skin.

Slowly she relaxed enough to put her arms around him feeling brave to have her bare breasts against his big, hairy chest. "There’s no rush," he said. "Only when you’re ready."

She was still feeling quite excited about the prospect of him looking at her tits. She had never shown them to anyone before. She had had a growth spurt when she was 12 but the growth had all been upwards not out. She saw other girls in her dormitory shorter than her with much larger breasts and they were always boasting about boys and teachers looking at them. She fantasised about boys looking at her bits but she’d come to believe that boys only liked big tits and no one would ever want to see hers. The look of delight and anticipation in Hamish’s eyes excited her.

Slowly, she dropped her arms to her sides, and took two steps backwards. She was not disappointed. His eyes widened with joy as he stared at her long legs, slender waist, and small breasts. "Beautiful," he said.

Reaching out, Hamish gave her breasts a gentle squeeze and then rubbed her nipples between his thumb and finger. Although her breasts were small they were very sensitive, as small tits generally are. "Nobody has ever touched me there before," she said breathlessly.

"In that case you’re going to really enjoy this," he said as he leaned forward and licked first one, then the other nipple circling his tongue around them. "Mmmmm, juicy little peaches," he murmured as he enjoyed his feast, sucking eagerly on her virgin breasts.

He stood up and looked her in the eye. "How are you feeling?"

She smiled shyly. Sucking her tits had made her a lot more horny than she’d expected. Having gone this far, she decided it was the right time to go further. "To be honest, I’m feeling a little overdressed." She gave him another shy smile as she unbuttoned her skirt, letting it fall to the floor and removed her regulation blue knickers. They were now both completely naked facing each other, looking each other up and down.

"Truly beautiful," he said in genuine awe. "You have the body of a woman and a little girl at the same time."

She liked that. She liked being considered a woman not a child. But at the same time he reminded her of her grandad and the times as a little girl when she used to play naked in the paddling pool in the garden while he watched. Perhaps that was why he watched so intently. Sometimes she would even come over and sit naked on his lap. She knew that he would look and admire her little body. He’d never done more than put his arm around her but she used to love her grandad’s hugs and his tickly whiskers when he kissed her as she sat naked in his lap.

"Now to continue your education, and since you used your mouth so expertly, I think it’s time I returned the favour and introduced you to what is possibly the most pleasurable experience known to man or woman." He got her to sit on his desk, then knelt down between her legs and put his mouth to her open pussy. She felt his beard against her legs, like her grandad's whiskers when he kissed her face.

He parted her lips with his fingers and applied his tongue to her clitoris. Waves of pleasure shot through her body like she’d never felt before, but he didn’t stop. He clearly knew what he was doing, as his tongue flicked and circled and swirled around her pleasure spot. She was still a virgin so he couldn’t insert his fingers, but he rubbed around the lips and the entrance to her hole. She was in heaven. He was right she had never experienced anything like it in her life. Her eyes rolled back in her head as she pushed her hips and her pussy against his tongue.

Very quickly she felt herself rising towards an orgasm, waves of pleasure flooding her senses, but when she had her climax he didn’t stop. He carried on gently licking until she felt she was going to explode. He speeded up again until she had a second and third, and then a fourth orgasm. Only then did he stand and put his arms around her kissing her on the mouth and the neck. She was exhausted. "That was a beautiful experience," he said. "I’m glad I was the one to introduce you to the amazing beauty of oral sex."

They hugged like that for a few minutes, as she let the waves of pleasure swim throughout her whole body. Then she looked him in the eye and said slowly and deliberately, "now I want to know what sex is like. I want you inside me."

"Are you sure about that? It’s a big decision and it will be painful to start with."

"I know. But Yes, I want to know what it’s like and I want you to be the first, I feel safe with you and you are a good teacher." He smiled inwardly at the irony that in a school full of teachers he was a caretaker.

His cock was still hard, and he pressed the tip of it against her hymen. "It will hurt but just at first?" She nodded. "I will do it quickly and then I’ll stop. And when you’re ready we can carry on to the pleasurable bit."

She looked him in the eye and nodded again. He hugged her tightly and then suddenly thrust his cock into her. She felt a sharp stabbing pain. With his cock inside her, he stopped and hugged her again. Then looking her in the eyes, very slowly he started to move in and out. The first few movements felt sore, but after that the pleasure returned, and she realised she was actually fucking for the first time in her life. She was no longer a virgin, she thought to herself with a smile. She put her hands behind her on the desk, leant back and enjoyed the sensation of his beautiful cock moving inside her pussy, still aware of the earlier sensations of whole-body orgasm.

He likewise was relishing the sight of her beautiful, slender body, small tits and his cock between her wide-open legs and the feeling of her tight cunt. He felt like coming very quickly but did his best to hold it back, moving slowly and sensuously, until eventually he could hold it no longer and speeding up he thrust deep inside her, shooting his sperm into her. He thrust again and again as he ejaculated into her. At the same time she shuddered as yet another orgasm flooded her body.

He drew her to him and put his arms around her again. It was just what she needed to be hugged and comforted by this big, bear-like man, reassured that everything was good. She felt happy. They stayed in beautiful embrace for several minutes, his cock still inside her.

Eventually, it was time to part. He withdrew from within her, and passed her some tissues to mop herself as he cleaned his cock. They couldn’t stop looking and smiling at each other as they both dressed.

"I really enjoyed that," he said, "and I’m genuinely honoured to be the one you chose to be your first. There’s lots more to teach you if you would like to learn. Or if you just want to come and sit and talk and have a cup of tea. You’re welcome to come back here any time."

"Yes, I would like that," she replied.

She departed, drifting down the corridor with a wide smile on her face, planning her next visit to the caretaker and wondering what else he would teach her.

3,331 Words.

This was a fictional story by Orange Squash. I'd be interested to receive feedback from any women with views on whether I have adequately described the viewpoint of women in my stories. You can email me at orangesquash59@gmail.com if you would like to comment on this story

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