The girls were sitting around in the café drinking coffee. They were all 17 or 18 and on summer vacation about to start their final year at school. The place was a bit shabby, dimly lit with plastic table covers but it was cheap and a favourite haunt of the youngsters.
The topic of conversation was sex, as it so often was.
“It was still in my mouth when he came!” Explained one describing a steamy session in the back of her boyfriend’s car the night before.
“I think I will have to go on the pill – we’re spending a fortune on condoms and I so much prefer doing it bareback.” Boasted another, and so it went on.
Anastasia always felt left out of these conversations as she had no experiences of her own to share. She lived with her Dad and Stepmother nearby in a rented run-down house. They had hardly any money, especially after her parents’ divorce and her Dad’s remarriage the year before. Anastasia desperately wanted to train as a doctor but the college fees and expenses would be crippling. She had worked all summer six days a week at two jobs to save some cash for her education and to contribute to the family budget so had little time for boyfriends.
Anastasia’s parents were Russian and they had emigrated when she was seven. She soon settled into her new environment. She quickly learnt English, but never lost her Russian accent. As a child she was not particularly pretty, but this changed as she became a teenager. She was now medium height, a good figure, long blond hair, fair skinned and with perfect size C breasts. She could not spend much on clothes but she had a good eye for fashion and made the most of what was available in her local charity shops. She knew she was attractive, but never had the time to cultivate boyfriends as her jobs and studies took all her energy.
That weekend her parents were away seeing her Dad’s sister and husband, uncle Toby. She did not want to go because Uncle Toby groped her breasts at the Christmas party last year. Uncle Toby was overweight, balding and had bad breath and she found him disgusting before the incident, now she never wanted to see him again. Fortunately John, the minister’s son, provided a perfect excuse to miss the family visit when he asked her to help with the Sunday-school picnic that he was organising. She gladly accepted so she could avoid her lecherous uncle Toby. The afternoon was turning to evening when the last picnickers drifted away leaving John and Anastasia to finish clearing up. Anastasia reached into her bag and handed him an apple. He smiled at her and accepted the gift.
“It’s a lovely evening so let’s walk back along the river”, he suggested as they munched their apples. She know he had a reputation with the girls, but she liked him so readily agreed. Once round the bend of the river, he stopped and gently kissed her; she didn’t try to stop him. His hands drifted upwards and he began stroked her breasts, gently, not like the rough groping of uncle Toby. She didn’t try to stop him. His hands lifted her tee shirt so he could feel her breasts over her bra but this was not the clumsy fumbling of an inexperienced teenager. Anne, the dowdy 51-year old church-choir leader had taught him well, when she took him into her bed the previous winter, and given him lots of practice. Next, his fingers found her bra clasp and he expertly undid it allowing him to stroke her breasts causing her nipples to grow; it felt so good.
He paused from their kissing and asked: “Make love?”
She was half expecting this, but she said nothing and just nodded. They walked away from the path and into a wooded glade where they found a patch of dry grass to lie on. He quickly took off the rest of her clothes and undressed himself then they laid together on the dry grass. She had never been naked with a boy before. She had butterflies in her stomach as she felt both nervous and liberated being like this with him. He took a condom from his pocket and put it on the ground next to him.
“We don’t want any little accidents, do we?”
She was relieved that she would not have to worry about getting pregnant. The embarrassment she felt when she was first naked disappeared when he began kissing her; being like this with him, it just felt so right. She had never seen a man hard before so she was surprised how big he had become and she wondered how it would fit inside her tiny pussy.
They kissed again and it felt wonderful embracing each other feeling his naked body against hers. She expected him to fuck her straight away but he didn’t. He kissed her breasts and licked her nipples. One hand and slipped between her legs, finding her wet pussy with his fingers. He found a place to stroke gently which gave her wonderful tingling feelings inside. Next he was kissing her stomach then he started gently licking her sensitive spot while his fingers entered her pussy and stroked her just inside. Her body quivered and shook and she screamed with pleasure as she experienced her first real orgasm. He paused briefly to kiss her then made her come again, then again. She didn’t try to stop him.
He expertly rolled the condom over his hard cock and she spread her legs apart to let him in. He slid over her so he was lying between her legs. She felt his cock probing the entrance of her wet pussy and it began to slip inside her. It felt tight, but not painful, as it slipped further and further inside her. He began thrusting, gently at first but then more vigorously which felt wonderful. He paused several times to kiss her passionately before continuing with their love making. This seemed to go on for ever before he finally exclaimed: “Yes! Yes!” and filled the condom with his spunk.
They lay together, cuddled and kissed then dressed and walked to her house, which would be theirs for several hours. She cooked a quick snack for them then she took his hand and walked upstairs to her bedroom. She moved her teddy bear form the bed. They stripped off each other’s clothes, lay on the bed to make love again. This was even better than the riverside session, Anastasia had discovered she really liked sex and could now enjoy chats about it with her girlfriends.
The summer drew to a close and John left for college. Anastasia was sad to let him go but knew that long-distance relationships didn’t last. Besides, having experienced sex with him, she now wanted to try lots of other things before she went to college herself the following year.
During her final year she had sex with several boys and one girl. The girl was one of her close friends. They had gone back to her place, while her parents were out, and had a couple of glasses of wine. Talking about boys and sex, with the booze, made them both really horny. As there was no cock available, they slipped off each other’s clothes, kissed and fingered each other before trying the 69 position to make them both come. This was a very special experience, and something she had dreamed about trying but not what she wanted to do regularly.
She quickly discovered that the boys who were brash and boasted about their sexual exploits were usually the worst lovers. She particularly liked fucking boys who were inexperienced, or even virgins, because she could control the pace of the encounter and she enjoyed educating them as John had done with her the summer before.
Then there was Alan, the class nerd. He was brilliant at maths and the teachers hated him because he would frequently challenge what they were trying to teach. It was during these intellectual duals, which he invariably won, that he felt really confident in himself and self-assured. He did not hang out with girls and was often branded as gay by his more unkind classmates. Anastasia did not think he was because he did not hang out much with boys either. Alan was tall and lanky with unkempt hair. He usually wore cloths that seldom matched and did nothing to improve his unattractive image. He was physically fit. He was a good runner and was occasionally picked for school sports teams, but maths was his passion.
It was the start of the summer term and as Anastasia was leaving school one Friday she met Alan who was also on the way home.
“Hi Alan, I’m glad I met you, I have a maths assignment I just can’t get my head around, could you help me?”
“Hi Anna, sure, what is it?” He replied
“My book’s at home, so could you come and take a look?”
“I would love to, but my parents are expecting me home”.
Alan’s Dad was a complete arsehole and bully. He gave Alan hell, always telling him to ‘Man up and stop reading those maths books’. Earlier in the year, he came to watch one of Alan’s games at school. Alan injured his foot and the coach pulled him off the field with what later turned out to be a broken bone. Alan’s Dad disputed the decision and in the altercation with the coach that followed he was dragged out of the school by the security guard, a large ex-marine, and banned from ever visiting the school again. Alan should have been embarrassed but everyone know what his Dad was like and most people sympathised with him.
Alan’s Mother was a quiet, usually quite timid woman. Although she worried a lot about her son, she had much more faith in Alan’s future than his Dad and did not see any reason to discourage his interest in maths. Whenever she stood up to her husband, he would lose his temper and rant about what a pussy he was and blame it on her for being too soft.
“Give them a call and tell them you are hanging out with some guys”, Anastasia suggested. He took his phone out of his pockets and spoke to his Mother – she did not mind and was pleased he was socialising.
They got back to her house and went in. Anastasia’s Dad and Stepmother were away for the weekend. They needed some private time and realised Anastasia sometimes needed the house to herself. Anastasia’s Stepmother was very noisy when she was making love. The house was small with thin walls and Anastasia’s bedroom was next to theirs so she could always hear them. Anastasia was pleased her Dad had got his sex life back after an awful time he had with her Mother over the last few years. Anastasia found listening to their lovemaking was very arousing and she would finger her own pussy to silently bring herself to a climax while they were doing it.
Alan and Anastasia sat at the table, plain brown wood from a cheap furniture store and surrounded by four matching rickety chairs.
“My book is upstairs, I’ll just go and get it. “ She told him.
As she entered her bedroom, an idea came into her head. She smiled to herself and undid the top two buttons of her blouse, revealing her cleavage. Back downstairs, after they shared a snack that Anastasia prepared, Alan took her though the mysteries of Geometric Series. He was a really good teacher. He started right from the basics and after half an hour she really got it and started to understand maths was more than just following formulas. While he was talking, she noticed him taking furtive glances at her breasts. She ignored this, for now.
“Let’s sit on the sofa, it’s more comfortable than these chairs. Would you like a drink?” She asked when they had put the maths books away.
He sat on the sofa and she went to get a couple of cans from the ’fridge. She bent down when she handed him his can so he could not help getting a really good view of her cleavage.
“Do you like them?” She asked softly, touching her breasts.
He turned bright red. “I … I …I’m sorry, I didn’t mean to …”He stammered.
“I don’t mind.” she said sweetly as she sat on the sofa right next to him. “When I was growing up, I was afraid my breasts would be really small or big and ugly, but I they are just right don’t you think?” She continued. He was speechless having never had this type of conversation before.
“Tell me.” She went on in quite an innocent voice. “Have you ever touched a girls breasts?”
“No … No .. I mean … only by accident.” He stammered, now feeling really uncomfortable with the turn of events. He was very happy to talk to her about maths, but this was a whole new ball game. One part of him wanted end the conversation, run out of the house and escape, but another part of him wanted to stay. He had never been alone with such a beautiful girl.
“That’s shame”. She said taking his hand and placing on her blouse above her breasts. He did not move his hand.
“Go ahead, explore a little”. She encouraged him which he did. She leant forward and kissed him on the mouth, while he felt her lovely breasts. The kiss was clumsy but she knew he would soon learn.
His mouth was dry and he tried not to reveal that he was shaking and his heart was pounding. They continued kissing and she let her fingers gently explore his trousers until she found where his cock was. It was big! Up until then, she thought she would just pet with him, but now she felt really horny and she had to have that cock of his, right now, before anyone else got to him!
“Shut your eyes, I have a surprise for you”. She commanded. He squeezed them tight shut.
She quietly slipped off her blouse and bra. “No peeping now!” She told him and took his hand and put it on her naked breast. His hand recoiled as if he had received an electric shock and he opened his eyes wide.
“Oh God!” He exclaimed. “I think I had better go, my parents will be worried about me”.
Actually, his parents were having a furious row. His Mother was worried about him and his lack of sociability, but his Dad said it was all her fault that he was such a wimp. “One thing we know for sure, he’s not out fucking girls, like he should be at his age.” He sneered.
Anastasia pointed out that his parent could call him if they were worried. She took his hand again and encouraged him to stroke her breasts again. By now, her nipples were hard and her pussy was getting very wet as she anticipated what they would be doing. As they continued kissing, she slipped off his shirt so his hairy chest could rub against her body.
“I’ve got another surprise, shut eyes if you want it.” She told him. He nodded and shut his eyes again. She slipped off the rest of her clothes, took his hand and places it on her breasts again. “No peeping yet.” She commanded.
Then she slowly slid his hand down, across her stomach until it was on her wet pussy. He kept his eyes shut.
“Are you .. are you naked?” He asked incredulously.
“Take a look.” She told him.
Once again, he was speechless. It was the first time he had seen a naked girl but he liked what he saw. He tentatively began to explore her pussy with his fingers and she smiled approvingly at him.
He wondered if he was dreaming this and, like so often lately, whether he would wake up and have to go to the bathroom to clean the semen from his pyjamas. But this was no dream.
“Your turn to give me a surprise now.” She said, shutting her eyes and pulling down his trousers and pants. She reached for his cock, which was now fully hard, and opened her eyes. It was very large, the biggest she had ever seen, nearly 10 inches long and perfectly proportioned.
“God, what a great cock.” She told him, making him feel embarrassed, but he did not try to hide his member from her. She lay down full length on the settee and pulled him down on top of her so she could kiss him and stroke his cock, carefully so he did not cum. She spread her legs as wide and guided his member toward her open, wet pussy. She had condoms in her bedroom but there was no way she wanted to stop what they were doing to get them. She rubbed his cock on the entrance of her pussy then slowly it started to slip it inside her.
“Please, please don’t come too soon!” She thought to herself.
Alan was breathing quickly with short breaths. His felt his heart pounding in his chest like it was going to burst. He felt both terrified and excited about what they were doing but he continued to push his cock inside her. At first her pussy was very tight, but once it got past the entrance he slipped in easily the rest of the way. First half way then with a few more thrusts all the way until their pubic bones touched. It felt really tight inside her but absolutely blissful.
“Fuck me Alan, fuck me!” She cried but he did not need to be told as he began thrusting in and out of her quicker and quicker. She soon reached orgasm and the muscles contracted round him but he did not stop. She screamed with pleasure then again as she felt his cum squirt inside her. They kissed as they savoured those special moments together. She gently extracted his penis from her. His cum began oozing out of her pussy so she grabbed the paper napkin she had used for the drinks to stop it staining the sofa.
“I’m sorry.” He said. “I did not mean to .. mean to..”
“Come inside me?” She said, finishing the sentence for him. “Don’t be silly, that’s what’s supposed to happen!” She said smiling, “and it felt absolutely wonderful when you came. We should have used a condom, but don’t worry, I’m taking The Pill so nothing will happen”. He looked relieved.
He reached for his shirt, but she stopped him. “They haven’t rung you yet and I want to spend a bit more time naked with you, it feels so-o-o good!” He didn’t disagree, but she was already thinking about round two.
They chatted for over an hour. This was the first time he had talked to someone for so long and he gradually opened up about how he felt about himself, his relationship with his parents and he even disclosed that he had felt really scared of rejection so avoided getting close to anyone, especially girls. She was a good listener, but she gently told him that naked he was really good looking, but he hid that with his poor choice of clothes and especially his hair cut did not do the best for him. She made some suggestions about how to improve his looks, when clothed, how to approach girls and how to deal with rejection if they did not want to talk to him. She was concerned about his relationship with his bully of a Dad and asked if he had ever stood up to him, which of course he hadn’t.
Part way through, he asked if she would be his girlfriend. She know she had to let him down really gently if she was not to spoil the evening.
“I really like you but in a couple of months we will both be off to colleges hundreds of miles apart and long-distance relationships never work. Also, you need to spend time getting to know more girls and maybe sharing a bed with them, so we can still have great sex when we want and who knows what will happen when we both finish college?”
He knew this made sense and although he was sad this would not be a permanent relationship he has pleased she had left the door open for future meetings like this. She took hold of him and kissed him gently while reaching for his cock which was growing hard again.
“Another surprise for you.” She said.
He shut his eyes. She bent down, took his cock, which had grown really hard again, in her hand and slipped it into her mouth. He gasped, but did not resist. She began gently sucking and licking it, which aroused them both further, and she began to taste his pre-cum juices.
Just then his phone rang! “Shit, it’s them”. He said with anger and frustration in his voice. He answered it.
“Hi Dad”
“Where the hell are you, you are supposed to be home by now!.” He shouted.
“I’m still hanging out with my friends.” He replied.
“Don’t give me that shit you haven’t got any friends, you come home right now!” He yelled.
Anastasia looked worried, this was the end of their lovely evening she thought and she so wanted him to fuck her again. He looked back at her beautiful naked body, those lovely breasts, partly covered by her long blond hair, and the triangle just above her perfect little pussy. He looked into her eyes and guessed what she was thinking.
“Dad.” He said in a firm voice that Anastasia had only ever heard him use when he was arguing a point of maths with his teachers. “I am an adult and I will come home when I am good and ready”. Anastasia was shocked that he had the guts to speak this way to his foul-tempered Dad.
“I demand to know what you are doing!” Shouted his Dad at the top of his voice.
“It’s none of your business what I am doing.” He replied in the same firm self-assured tone, “but I will tell you anyway.” Anastasia was now even more shocked. “I am with a beautiful girl right now and she wants me to stay the night with her and that is exactly what I am going to do.”
For the first time ever, his father was at a loss for words, so he just put down the phone and turned to his wife who had tears running down he cheeks. Maybe she did not need to worry so much about her son after all.
Anastasia hugged Alan tightly, kissed him passionately and also cried. “That was awesome, well done you!” She exclaimed.
“Let’s go to bed; I think this could be a very long night.” She giggled.