Tom's First Time

Some years ago when Tom was 18 something happened to him which had a significant effect on his life. It was his sexual beginning. Okay he'd started masturbating at around the age of thirteen but this was more significant.

He was painfully shy throughout his teens particularly around girls. He had attended an all boys school which hadn't helped. But after leaving school early at 16 he had started working in an office where the girls were all older than him and, whilst he wanted to interact with them much of the contact involved teasing. He couldn't duplicate their carefree attitudes and words, the teasing was all one way. They laughed when he blushed which made him blush all the more. He lived in a village and had joined the local youth club.

There were girls at the youth club but Tom had not made much progress there either. Other village lads seemed to have no difficulty. He had started to climb mountains with one or two of his school friends travelling on the bus into The Lake District, a mountainous area near his home in the north west part of England. He loved the fells and when an opportunity arose he jumped at the chance to have a weekend away from home amongst them. The National Park wardens were running 'Safety on the Mountains' weekends aimed at young people around his age. The mixed group of participants stayed at a youth hostel on the Friday and Saturday nights.

Tom had heard a rumour that boarders from Kendal High School, a girls school in that area, would be going on the weekend. He hoped that he might get an opportunity to engage in conversation with these pupils. The weekend started with a short walk on the Friday evening.

"Hey Tom, did you bring any jonnies with you for the weekend?" a youth called Ian he knew vaguely from school enquired. They were at the back of the walking group out of earshot from the others.

Tom had an inkling about what he meant but was rather taken aback at the question.

"Jonnies?"

"Yeah, you know Durex, got any?" In those days the word condom had not become the universal name for the male contraceptive it is today.

"No, sorry, why do you ask?" He was trying to be casual about it. The truth was he'd never seen one in his life. He reddened a little hoping Ian wouldn't notice. Ian reached into his pocket and produced a couple of packets with the words 'Durex extra sensitive' on them.

"Just in case we get lucky." Ian said triumphantly, quickly putting them back out of sight. He winked and grinned at Tom.

Tom was flattered that he'd included him in his comment and did his best to relax and grin back. This was someone who was obviously experienced in a way he could only dream about.

"Good stuff." He said as confidently as he could.

The hostel turned out to be overbooked. There were not enough bunks for the boys. As it turned out Tom was the only boy without a bed. When Betty, one of the organisers of the weekend came to tell him that he was going to be spending the two nights in the area reserved for the girls he was more afraid than anything else. At least he had a bed for the night. The female area of the hostel was split off into smaller rooms with about three bunks in each. The woman saw the expression of alarm on his face. She was not unsympathetic.

"You'd better not sleep there all on your own Tom," she said kindly. She slipped out into the common room and he heard her shout "Ian, come here." in a loud voice.

"You've been walking together on the fells earlier so I presume you know each other." They both nodded. She explained to Ian what she had in mind.

"Now Tom I want you and Ian to promise that you will behave yourselves whilst you are in that area. We are putting you on trust to avoid all contact with the girls in the other rooms," Betty told the two youths gravely.

Of course they agreed to behave. Tom knew that Ian was delighted with this turn of events but his face was impassive in front of Betty. She looked quite old to the two eighteen year olds although in reality she was in her late twenties and quite a beauty. She wore a short skirt showing off her good legs. Her slim waist and large bust added to the pleasing effect.

"I'll bet Betty's a bit of a goer. I didn't see any wedding ring," Ian said as we prepared for bed later that night. He'd decided to let the girls make the first move so we were 'playing it cool' as he put it. Tom nodded and smiled. He was way out of his depth but still not letting on. He would allow Ian to take the lead and see what happened.

They didn't know what was said to the girls about leaving them alone, if anything. If they had made similar promises it seems a few couldn't resist the temptation to disobey. The youths had hardly got into bed when there was a knock on the door. Tom had signed up for the weekend in the hope of maybe finding a girlfriend but this was different. Ian opened the door and stood to one side to let in a girl of about eighteen in a baby doll nightie. He left the door slightly ajar and she was quickly followed by another two girls also in skimpy night attire. One of them with long black hair who seemed a little older than the other two closed the door behind her, locked it, and put her finger to her lips.

Tom had never even kissed a girl properly before but it was the girls who took the initiative. There were two bunk beds and one single bed in the room. Tom and Ian were seated on the single bed and in complete silence each girl moved between them kissing them in turn. The leader wearing the baby doll chose Ian, sitting on his knee and putting her arms around his neck. Tom was very conscious of his stiffening erection, these were beautiful girls who seemed supremely confident and had evidently got plans. He knew they were clearly a part of their plans and neither of them was going to back down.

Tom tried to look nonchalant without much success and was aided by the need to keep silent. It wasn't long before one of the other two girls, the blonde one, was sitting on his knee, her arms around his neck. He was learning fast, his first efforts at kissing were amateurish but he opened his mouth a little and tried again finding a darting tongue between his lips. He'd often had doubts about his attractiveness to the opposite sex but this girl was making it clear that she wanted him and he was flattered. He was hardly able to believe he was getting what he had always dreamed of without having to do anything.

He moved his own tongue forwards and she grunted encouragement. The tonguing seemed so rude, he realised that a part of him, his tongue, was entering her body. At this thought his member responded, jerking a little. Blondie felt it move opening her eyes, a giggle issuing from low within her throat. Tom could see Ian with his hands on baby doll's breasts. The girl without a partner was pinching her nipples and on seeing this he almost ejaculated, his penis at full stretch. He loved the scent Blondie was wearing and relished the taste of her lips and mouth. She broke the kiss and moved her lips to his ear. Her blonde hair had brushed across his face as she moved and he loved the smell of it.

"You can feel my tits if you like." she whispered.

She returned her lips to his mouth and they resumed exchanging tongues. Hesitantly he began exploring her breasts moving his fingers down her cleavage first, brushing a nipple with the back of his hand then doing the same with the other nipple. Her nightie provided no protection at all and soon he was tentatively squeezing her nipples one at a time. He could tell by her sighs that she was enjoying it. Their lips were now locked together. He stole a glance towards Ian and saw they had moved towards one of the bottom bunks and were slipping their night wear off. Baby doll was soon naked lying on her back on the bed. Ian, also naked, his cock erect, extracted a french letter from the packet and threw the rest towards Tom without a word.

Tom broke off the kiss and Blondie looked towards Ian and Baby doll and smiled.

"Take a look at what they're doing. Fucking great isn't it?" she whispered.

"Er... Yes, I....er...."

"You're new to this aren't you? Sweet sixteen and never been kissed?"

"Pretty much, eighteen actually." His face reddened, had he made a mistake admitting it?

"Well, actually," (she drew the word out deliberately slowly, mocking him), "I'd be delighted to show you the ropes. I came in here hoping for cock and don't intend to be disappointed." She reached inside his pyjama bottoms and pulled out the item in question. It was harder than it had ever been before. Tom forgot his nerves and stared back at her proudly.

"The staff at the high school keep us boarders in the upper sixth on a tight rein. We don't get many opportunities like this." She had put her mouth close to his ear again and spoke in the lowest whisper. Her breath on his ear made the hairs on the back of his neck stand up. He'd read about that in books but this was another first for him.

Blondie stroked his cock to check that he was primed and ready then moved onto the single bed slipping out of her nightie and panties. As Tom stripped off she picked up the packet and took out one of the rubbers..

"My boyfriend usually does the honours but it can't be that difficult can it." Sure enough she soon had it in place on his phallus. She laid down on the bed on her back and opened her legs wide. As he moved to kneel between her gorgeous legs she fingered herself, already anticipating what was to come.

"Just stroke it around the entrance to my cunt sweetie. She's nice and wet for you. Make sure your cock is nicely lubricated then push into her slowly," she instructed. He was clumsy and struggled to find her entrance. She took hold of his firm erection and manoeuvred it into place. "Not too fast at first, build up a nice rhythm. That's it. Mmmm.... That's the way, shove it up me right to the hilt. It's a nice tight fit. See if you can hold off from coming as long as possible. Most men I've been with finish too early."

He was concentrating hard, hanging on her every word, and this helped to calm his desire but when she stopped explaining and began moaning he knew he was becoming close to orgasming. He began to recite the seven times table in his head, one he'd always struggled with and it helped a little. But when Blondie began to orgasm herself it was impossible for him to hold back. He felt his sperm squirt inside the rubber sheath and the feeling was amazing, at the time it seemed a hundred times better than a masturbatory orgasm. He moved to lay on his side and kissed his blonde haired lover taking a quick look around after losing track of what was happening whilst he was inside her.

The dark haired girl was now sitting on Ian's knee kissing him whilst Baby Doll still lay stretched out on the bottom bunk where he'd seen her before. He felt quite content to lay there with Blondie snuggling together. His penis was now flaccid and he was not expecting it to rise anytime soon.

Blondie however had other ideas. She got off the bed and knelt down facing it.

"Move your arse. Sit on the bed edge facing me, let's see if there's any more life in that big cock of yours."

Tom had just successfully completed an epically important rite of passage. He was in a daze, shocked, but at the same time gloriously happy. His need for sex had been satiated, he would have been happy to turn his back to her and fall asleep. But he was essentially a pleaser. Never more content than when he was doing a good turn for someone else. Putting aside his own needs he moved to comply.

"Anything you say." he said casually.

She grasped his member and brought it up to her lips, licking the end. He felt it jerk a little and when she took it deep into her mouth, to his surprise he felt it begin to stiffen. He'd read about blow jobs, so dirty, a woman wanting to taste her own juices, licking the place where urine was expelled. But the very wantonness of it all was thrilling him. His todger thickened even more, rising almost to the length and thickness of a few moments earlier. She still had it in her fist as she wanked him and sucked on it. Slowly but surely it expanded to a point of full rigidity. Soon she'd made sure a second rubber johnny was in place.

"There you are, I knew you had it in you. Let's try a different position."

With that comment she stood up and leaned over the bed pushing her head into the bedclothes, her plump shapely bottom sticking up in the air. Standing behind her, he once again struggled to find her cunt hole but she reached around and helped him whilst his cock remained nice and stiff.

"Grab my tits to help your balance and fuck me harder this time. I don't mind if you're rough. Slap my arse and tell me I'm a dirty slut. I love it."

Tom found the position awkward at first. He slipped out a couple of times but Blondie was patient with him, reaching behind each time to make sure the fucking could continue. He made a halfhearted attempt to slap her shapely bum but was too inexperienced to call her names.

"Thank you." she whispered in encouragement. He hit her again harder as he drove his penis in and out. "Now you're getting the idea," she said.

He noticed she was stroking herself above her cunt as he fucked realizing it was increasing her pleasure. His knowledge of the female body was sketchy based on soft porn magazines and books available at the time. But he knew the word clitoris and decided she was stimulating it. It only increased his arousal, but this time he wasn't worried about spurting early. He was confident he could hold off this time despite the sexually charged atmosphere in the room. He increased his speed and squeezed on her nipples. She began making low grunting noises each time he bottomed out.

"That's it Tom, fuck me harder."

Ian glanced across at them and grinned. "Hey, keep the noise down," he said in a stage whisper. He was fully occupied fucking the dark haired girl. Baby doll was standing next to the bed they were using, her legs apart. Our other visitor had her finger in Baby doll's moist snatch making sure she wasn't left out.

There was another knock on the door.

The fucking in the room continued at a slower tempo. The five were determined not to make a sound.

Whoever was outside the door tried to open it, finding it locked. They knocked again.

Everywhere was quiet. Ian and Tom held their breath, straining to listen, until at last footsteps were heard tiptoeing away.

"Must have been one or more of the other girls." Blondie said quietly. She giggled, her fingers over her mouth to hold in the noise. Tom saw her move her hand to her crotch and start stroking herself again.

"Right Tom, put your back into it." Her words were so quiet he could hardly hear them.

His ardour had been slightly dampened but, spurred on by these words, he resumed his former speed. His cock was soon as hard as it had ever been. He could feel his climax building. Fireworks were exploding in his head. This was even better than the first time. He had a fleeting thought about Blondie wondering inanely if women orgasmed like men when suddenly she was jerking violently and, as he shot his load, he felt a liquid squirt from her cunt soaking the hairs around his penis. Her hand was back over her mouth again and he had his answer. Yes some of them did. She was trying to block out the sound she makes when she orgasms.

The girls left our room shortly after that. I think we all felt nervous after the knock on the door feeling we had been pushing our luck. Ian locked the door after them.

The following day and evening was busy with various activities and lectures including abseiling down a cliff and scrambling to the top of a high mountain. Tom was disappointed that there was no opportunity to spend time with the person he was calling in his head "my blonde girlfriend". He and Ian were taken to one side by Betty who had spoken to us the day before and asked about a used french letter found in their bedroom by one of the cleaners. Of course Ian denied all knowledge of it suggesting it might have been placed there to get them into trouble. Tom backed him up.

"I'm very disappointed with your behaviour. Some of my colleagues wanted you sent home. I spoke up for you and have volunteered to stay in your bedroom tonight to keep an eye on you. Look at me Tom." She tried to make eye contact but he looked towards the ground although she could see his face heating up. "I'm particularly surprised to find you in this situation. I trusted you and you've let me down."

Tom tried to start to say something but she raised her hand to stop him. "I don't want to hear any more lies. I've spoken to a few of the girls so I know about the party in your room last night." She smiled "The few I spoke to were annoyed they weren't invited."

Tom had managed to find out Blondie's name (Kathy) from his cousin Mary who was also on the weekend. Later he caught up to Kathy whilst they were out on the fells.

"Can I see you after the weekend is over?" He said still breathless. "You see Betty, one of the staff, is moving into our bedroom to keep an eye on us tonight."

"That's a shame! Well, maybe you could see me, but it's difficult. I'm going back home next weekend. It means I'll see my boyfriend. It's very frustrating not seeing him when I'm in Kendal." Kathy looks Tom in the eye and grins sheepishly. He takes this to mean the only reason he got a shag last night was down to sheer sexual frustration. "Oh, I see, I was hoping to become your boyfriend." He couldn't conceal his disappointment.

"Sorry, I'm taken." She giggled. "Wait though, do you have a car?"

"No, er.... there's my dad's, but I've not passed my test yet." He felt it was hopeless.

"Pity, you see they only allow us out on our own for four hours on a Saturday afternoon. We're not allowed to even talk to boys. Anyway, as I say, I'm not here next weekend." She pauses for a moment. "Wait, I've passed my test. Do you think your dad would let me drive his car?"

"I doubt it. I could always ask him." He brightened grasping at a faint glimmer of light. He was desperate to see her again as only a teenager without any previous experience with girls would be.

"If your dad's okay with me driving send a note to me at school through that cousin of yours, Mary isn't it? I'll see if I'm free in two weeks time."

"But what happens if he says 'No'?"

"Sorry Tom, it's not going to work without a car."

Tom and Kathy sat next to each other through the Safety on the Mountains talk that evening but there was no opportunity to talk and she seemed to be avoiding him after that. He realized that her interest in him was nothing like his interest in her. Without his dad's approval to her driving he'd already lost her.

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Tom is an only child and his parents separated when he was about ten years old. After they split he was with his mum at first but he'd felt like an unwelcome guest living in his stepfather's house. He'd moved back after a year to what he saw as the family home and had stayed there.with his father since then. His mum kept a room for him but he only stayed overnight there about once a month, despite seeing his mum regularly. His dad treated him well and he enjoyed living with him. His dad had never settled down with anyone in particular and was single when Tom was eighteen.

"But don't you see dad it's the only way I'm going to see her again." Tom and his dad were having one of their rare arguments. "This is my first girlfriend and I don't want to lose her."

"But she's got a boyfriend back in her hometown. Let's face it, she's only interested in my car not in you. How do you know she won't fill it with all her mates? You'll probably be stuck in the back with another couple of local lads. From all you've said she's had a lot more experience of boys than you have of girls."