Teenage Touching Chapter 3 - Ruperts Back Story

TEENAGE TOUCHING – RUPERT’S BACK STORY

This tells about Rupert’s past sexual experiences. All the characters having sex in this story are at least 18 years of age apart from some teenage nudity. Also, as this is fantasy, no account is taken of contraception or hymens.

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Now it was the girls’ turn to look bemused as Rob asked Angela to pull up Rupert’s underpants but leave his trousers pulled right down. Rupert was still tied tightly to the wooden stakes in the ground, unable to move with his arms to the sides and legs tied together, looking like a crucifix on the grass. Rob took a long roll of cloth from his bag, like an extra long scarf and proceeded to wrap it around Rupert’s head and face until it couldn’t be seen, leaving gaps at his nostrils and mouth to allow him to breathe. Rupert looked like he was ready to be mummified. “What’s going on, what are you doing?” protested Rupert, but Rob said only one thing, “just remember if anyone comes along you’re better off not being recognised.”

Then Rob took an envelope from his bag with the words, “READ ME” in large letters on the front, and tucked it into the top of Rupert’s Y-fronts.

The girls followed Rob as he picked up the remnants of their picnic and walked into the adjacent woodland, leaving Rupert alone, still staked to the ground, naked apart from his underpants.

Rupert was very confused as he lay there. Yes he had carried out the burglary, reluctantly, and that had led to him lying there, staked to the ground, unable to move, almost completely naked. And he’d just been wanked off by a girl he hardly knew as another watched and while Rob had taken photos to blackmail him.

Despite his arrogant reputation he was actually fairly inexperienced in sex. In eight years at a boys’ boarding school, the only sex he’d had was some adolescent experimentation with a few other boys, but no girls. At least University had given him the chance to lose his virginity and fuck around but he’d always selected the most naive virgin girls who easily believed him when he said he loved them. Consequently he’d never learned any manners with women. 

He hadn’t even seen a naked female till he was at Uni although it had happened when he was back at home one weekend for his dad’s birthday on the Saturday. He got back on the Friday and his parents went out to the pub as they did every Friday evening. His sister Sally was four and a half years younger than him and she had some friends over for a sleep-over. 

Rupert noticed that Sally had raided their parents’ drinks cabinet and the girls were all getting a little tipsy. There was a pair of identical twins Cindy and Sally. They were Barbie lookalikes, tall with wavy blond hair. There was a stylish Italian girl, shorter with long black hair, and a couple of chubby girls. The presence in the house of five additional females almost kept his curiosity but he snobbishly felt he was too old for them and besides Sally was his annoying brat sister. 

So Rupert had tried to stay away, but to them he was an attractive older boy and potential ‘catch’ and it was clear that the Italian girl, Clara, fancied him in her quiet sultry way, looking at him with big brown eyes under long eyelashes. He tried to avoid them, moving from the kitchen to the living room but they followed him. 

Taking confidence in being a group, and with the alcohol kicking in, they all kept giggling and trying to attract his attention. The Barbie twins were obviously the leaders of the group and kept flirting with him and making suggestive comments which he pretended to ignore but which actually made him quite aroused.

“Clara fancies you,” blurted one of the twins. 

“No I do not,” said Clara going red.

“She said she wants to suck your lollipop and have your babies. But you’ll have to be gentle she hasn’t done it with anyone before.”

“Stop it,” shouted Clara going even more red and hitting the girl with a cushion. “It’s you, you want to have his babies.”

“I don’t want his babies but I’d like to see his lollipop” said the Barbie twin. They fell on the sofa laughing, but Clara kept looking to see his reaction.

But they kept on teasing him. “How many girls have you had?” asked one of the twins.

“I’ll bet he’s had loads, tall, quiet and handsome,” said one of the chubby girls.

“I’ll bet he’s got a big prick”, said another.

“Yeah, looks like a huge package”, said the second twin.

His sister didn’t say anything but she joined in the laughter and shot him glances occasionally to see how he was taking it. 

Rupert’s didn’t respond, trying not to go red, embarrassed to be reminded that he’d never had sex, not even seen a naked girl. 

He wasn’t used to being the centre of attention and having girls make suggestive comments, even if it did sound a bit adolescent, clearly not knowing what they were really talking about. How did they even know these words at their age, he wondered, forgetting that at their age he’d been experimenting with sucking cock. But all the attention was making him very horny.

He sat on the sofa to try and ignore them but the twins pushed Clara towards him and she fell onto his lap. Shocked, he helped her up but the sudden proximity of her slight feminine body and the sight of her Latin face, long black hair and wide, dreamy eyes right in front of him aroused a lot of emotions.

Eventually he went upstairs to his bedroom. He would have locked the door but his parents didn’t believe in locked doors except for the bathroom so there was no key. He sat on his bed trying to ignore the loud laughter downstairs. 

Soon he heard them all come up and go to his sister’s room, which was next to his. So now the noise was inescapable and it sounded like they were still drinking as they got ready for bed. He couldn’t help imagining them all getting undressed. He wanted to ignore them but part of him wanted to be in there, drinking with them and flirting, despite the age difference. 

After a while he heard voices being raised like an argument. Soon he heard a loud commotion spilling out of Sally’s room and along the corridor. Suddenly his bedroom door burst open and in stumbled the Barbie twins dragging the Italian girl Clara, one on each arm as she struggled to escape. The other girls stood behind them in the doorway watching. 

He couldn’t help noticing that the twins were now in their nighties, which were very short, coming to just below their panties, showing their long slender Barbie legs. With a low neckline and sheer material, the nighties left little to the imagination for the shape of their tits and colour of their nipples, which jiggled around as they struggled with Clara. 

But more striking than that, Clara was totally naked. They’d dragged her in for him to see. 

She was shouting at them in Italian with what sounded like a lot of swearing. One of the twins said, “We just wanted to tell you that Clara still fancies you and we thought you’d like to see what you could have if you wanted. She’s all yours, what do you think? Sorry her tits are so small.”

Clara was frantically struggling but couldn’t escape the taller girls’ grip. “She’s a bit fiery,” said the other twin, “but if you want we’ll hold her down and you can have her now.”

Rupert’s eyes widened as he contemplated the prospect of shagging the gorgeous Italian girl right now on the carpet while the beautiful Barbie twins held her down.

But then the twins let her go and she ran out of the room and Rupert was left with her naked olive-skinned body, her tits and her slit engraved on his eyes. 

“That was our little present to you from us,” said the twins, giggling at his dazed, open-mouthed expression. 

Then one of them lifted her nighty right up, revealing her pink panties with yellow flowers. “And if you don’t want her you can have me,” she said and they all turned and left the room giggling. Rupert was left wondering whether their offers were real or were they just teasing him.

Of course, after that, seeing a naked female for the first time, he got an instant erection. He’d spent countless nights at boarding school wanking himself off as he tried to imagine what it would be like to see a naked girl and now he had. He desperately needed a wank right now but he daren’t do it in his room with no lock. They might come back in. He decided to have a bath, which was his favourite place for wanking.

He ran a hot bath, making sure to lock the door. It was an old Victorian house and the lock was a large rectangular affair with a big metal key which he turned a full rotation to be sure it was locked. Then he undressed and got into the bath. He lay back and started stroking his cock, which was still hard, remembering every detail of what he’d just seen, her long hair reaching down to her nipples, her waist, her bald slit… he was on the point of coming when he heard commotion out on the landing again.

“Are you in there lover boy?” He recognised the voice of one of the Barbie twins. He heard the door handle being tried. “Your girlfriend wants to come in and join you in the bath.”

“Go away”, he said, suddenly petrified. “The door’s locked, you can’t come in.”

“Your girlfriend says she wants to see your sausage. She wants to lick it.”

“No I did not,” said a voice, clearly Clara’s, indignant but also laughing.

“She wants to put tomato ketchup on it and suck it”

“I don’t. I didn’t say that.” 

There was a pause and he heard lowered voices from the landing. He tried to make it out. He heard snippets, “I know how to do it, it’s like ours at home, we just need a coat hanger and a sheet of paper.”

There was quiet for a while and then he saw a sheet of paper being slid under the door. He saw the door key jiggling, somebody was poking it from the other side. Then the key dropped out of the lock and landed on the piece of paper. Slowly the paper was withdrawn under the door, pulling the key with it.

“Got it,” said a twin loudly, and in a moment the door was unlocked and all the girls spilled into the bathroom, with more shrieks and giggles as they saw him sitting in the water naked. He put both his hands over his erection, finding that it’s difficult to completely cover a large hard cock with two hands, especially since they were now right up against the bath. The girls were pointing and giggling.

“He came in here to play with himself,” laughed one of the twins. “Go on Rupert, don’t let us stop you, knock one out. We’ll applaud when you finish.”

The Italian girl, now in her nightie, was beside the twins staring intently. The two chubby girls were behind them trying to see. And there was his sister Sally, even she was trying to get a look.

“Get out, get out,” he shouted, but they ignored him. 

The twin lifted her nighty again, several times in succession, showing him her panties flirtatiously. “Do you like my pink panties, lover boy?” she laughed. “If you don’t want Clara you can take my panties off.”

Clara gasped and hit the girl indignantly and while she did the other twin grabbed Clara’s nighty and lifted it to reveal her white lacy panties. “Clara said she wanted to feel you prick in her fanny”.

“Stop it, no I didn’t,” said Clara glaring at her and going very red again, but then she laughed. It seems they’d made friends again and Clara blushed as she looked back at Rupert, glancing down at his hands as he desperately tried to hide his erection.

One of the twins grabbed Clara again and pushed her towards the bath. Losing her balance she was on the point of falling on top of Rupert again, so to stop her he had to reach out and push her shoulder. But that uncovered the top half of his cock and Clara, almost on top of him got a clear view of it till her could cover himself up again.

“It’s big alright,” said one of the chubby girls.

“What else do you want to see?” asked the other twin. “Some boobies?” She pulled the other chubby girl forward. Instead of a nighty she had on shorts and a camisole top. The twin grabbed her top and lifted it up revealing a pair of well developed round tits. While the girl gasped and tried to pull her top down the other twin grabbed her shorts and pulled them down to show a hairy bush. The girl shrieked and laughed before turning herself away. 

They were all laughing, totally confident, being six of them together and quite tipsy, just having fun. Even his sister Sally was laughing with them.

Rupert was shocked but excited. He’d never been the centre of girls attention before. He was enjoying them looking and flirting and that was keeping his cock rock hard. But he was very aware that he was sitting there naked in water that was quickly getting cold. He couldn’t stay there forever.

He decided that the only way to get them out was to do it physically. Putting his shame to one side for a moment, he suddenly stood up, splashing water everywhere, his erection standing proud, and got out of the bath. He spread his arms wide and ushered them out of the door, “Get out, get out, get out,” he shouted.

The girls shrieked even more seeing his upright cock bouncing left and right as he moved. Clara was looking at it lovingly. He was most embarrassed that his sister was looking at it too. But his intervention worked and soon they were all out. He locked the door again and removed the key, knowing he was now safe.

It had been his introduction to seeing a naked girl and also the first time any girl had seen him naked. Definitely a night that stayed in his memory.

After that weekend and back at Uni, those memories sustained him for many more wanks and made him even more desperate to see more naked girls and to lose his virginity. He tried hard in the campus bars to chat up girls but he didn’t get very far. He discovered that he had more success chatting up girls who were younger than him, or girls who were more impressionable and naive. Even in his third and fourth year he went for the freshers. They were more likely to believe him if he told them they were beautiful and he loved them. 

Eventually he got his end away with a girl who looked innocent but clearly wasn’t a virgin herself. After he’d shagged her, he asked how many boys she’d had sex with and she lost count at 15. And she’d included some girls names. From what she told him it sounded like she’d been shagging for years at school and often with much older boys, even a teacher. Even a friend of her dad’s! She said she liked older men because they were better at sex and they liked her because she had a naturally wide-eyed innocent expression.

Once he’d lost his virginity, he found it easier to pick girls up and some of them clearly were virgins and needed a bit of coaxing and persuading. He wondered sometimes if he was too pushy, but he convinced himself they enjoyed it too and he wasn’t doing anything illegal. Everyone at Uni was looking to get laid, he told himself.

After he’d finished four years of University he moved home. Girls his age didn’t seem to be interested in him so, again, it was his sister’s friends who he turned to. At least they were older now. On one occasion, some of them had come round to use the swimming pool in the privacy of their large walled garden. It was hot summer. They had all arrived dressed in short skirts and then stripped down to their swimsuits or bikinis to play in the pool. Sadly neither Carla nor the Barbie twins were there, these were quieter, less rowdy girls.

He had placed himself in a deck chair by the pool and pretended to read but really he was looking at their suntanned legs and their tits jiggling in their bikinis. He liked the way the big tits wobbled and the small ones jiggled. He had to position his book to hide the hard on in his shorts. 

The girls pretended to ignore him. In reality, as before, they were well aware of the presence of an older boy and splashed around in the water showing off. But he got the impression they were all quite naive. He wondered whether any of them had ever seen a cock before. It made him so horny he was desperate to see their tits, to see them naked. He wanted to fuck them all. But there was one in particular he really liked. She was petite and attractive with shoulder length blonde hair, wide eyes and a permanent smile. And she had the smallest yellow bikini barely covering her small tits.

So when she went indoors to use the toilet, he followed her. The only toilet was upstairs across the landing from his bedroom. When she came out of the bathroom, he invited her into his bedroom to listen to a record. She accepted, flattered by the attention from a tall good looking lad just back from university. 

So there they were in his bedroom, he just wearing shorts and she in her tiny yellow bikini and big innocent smile. He was horny as fuck.

Once in his bedroom he’d shut the door and pounced. He put his arms around her holding her tight. He told her he thought she was really beautiful and he’d fancied her ever since he saw her, and he meant it. He started kissing her. 

It was so unexpected, she was shocked. But he persisted and eventually she went along with it, kissing him back, seduced by his words of love.

His hands were all over her, first her hair and neck, but then quickly moving onto her little tits. She wriggled out of his grip and went to look out of the window at the others playing by the pool. But he came up behind her and put both arms around her waist, kissing her neck and shoulders and ears. 

Then he again put his hand on her tits, reaching round from behind. She tried to remove his hands but he was stronger and quickly pushed her bikini up to expose her tits and squeeze them with both hands. She’d never had anyone touch her intimately before and the feelings in her body were overwhelming. She’d turned round to face him again and they kissed.

Now he wanted her to see his cock, like those girls had seen it in the bathroom. So while they were kissing he quietly pulled it out and placed her fingers around it. She looked down and couldn’t believe what she was seeing. She wanted to look away, but she couldn’t stop looking down at it. He put his hand around her fingers and helped her wank it. He kept on squeezing her tits and telling her how beautiful she was as his hand kept hers stroking his cock up and down, then he took his hand away and she carried on. He loved seeing her delicate little fingers around his cock. And even though it was totally unexpected, she liked feeling his manhood in her hand, it made her feel special.

She felt like she was quickly falling in love with him, she’d never been this close to a boy before and the sensations flooding her body were so intense. When he pushed his hand down her bikini bottoms, she tried to resist but his fingers quickly found her slit and he pushed one finger deep into her hole. At that point she was lost to him. It felt too good.

As he started to fuck her with his finger she draped her arms around his neck and gave in. She was sure they were in love with each other and it felt amazing. He continued fingering her until she screamed and came. It was the most intensely pleasurable experience of her life. 

But he wanted more. He wanted to feel her naked body beneath him. He wanted her virginity. He kept telling her how much he loved her. He told her that since he’d made her come now it was his turn as he pulled her down onto the bed and pulled her bikini off altogether. 

Naked and still reeling from her orgasm she didn’t have time to think as he lay on top of her and pushed his cock into her wet hole, into her place that no cock had been before. Lying on top of her little frame, seeing her tits, feeling his cock in her tight twat, it took him no time to come.

Of course just like the girls at Uni, once he had finished, the thrill was gone. She wanted to hug him and talk of love but to him she suddenly felt like a silly little kid. After a few minutes hugging, he ushered her out of his bedroom saying he had things to do. She went back down to the pool, her mind reeling with emotions of love and sex but she felt confused, ashamed and didn’t tell anyone what had happened.

A few weeks later, another of his sister’s friends visited for a sleepover. He found her at night wandering on the landing in her nighty. He’d invited her to his bedroom and did the same thing all over again.

Eventually, the girls talked to each other. Word got round and his sister’s friends stopped coming to the house.

So now, as he lay there on the grass, tied tightly to stakes in the ground, having been groped and masturbated by those girls, all these thoughts and memories were suddenly swirling around his head. When Rob had accused him of burglary, which he had done, he was ashamed. But then he’d also accused him of shagging defenceless girls, and it had made him think. Was that true? He always thought they’d been willing participants. “We’re all adults,” he’d told himself.

He lay there, still with a scarf around his face and eyes, and wondered what was going to happen next.

(CONTINUED)

[Author’s note: a lot of these events are inspired by real experience. The flirtatious teenagers are based on real girls I knew when I was 21, and the girls dragging a naked Italian girl out to be seen by the boys really happened, outside the swimming pool changing rooms, in my last year of junior school.]