Claire and her Boss, Simon

It was near the end of a hot summers day. Simon tried to concentrate on welcoming his group of new female staff in the company lecture theatre. They were near the end of their six week induction program and he knew that there had been a lot of hot partying and friendships formed during that short period. As he looked up at the girls in the tiered seating above him, his mind kept wandering. All he kept thinking about was their emerging sexuality – long toned legs, firm breasts, pretty faces and luscious lips.

He imagined some of those lips around his fat cock. Especially Claire, the stunning, girl sitting in the raised front row, about level with his face. Her skirt was so short he could see most of her thighs and her white cotton panties. He was sure her pussy would taste like sweet honey. Even though she was 18, he wondered whether she was still a virgin and, if not, who was the lucky guy who had taken her cherry. His cock was already half swollen and suddenly twitched in his trousers as it grew another inch..

Unbeknown to Simon, several of the girls were watching Simon and could clearly see the outline of his fat cock. For an older guy, he was hot and obviously well hung. Two girls in the back row were not wearing any panties and had their hands between each other’s thighs, slowly masturbating each other. Just after seeing his cock twitch in his trousers, one of the girls came and her sticky juices flooded over the fingers of her friend. She licked them off slowly and smiled at her friend. They would continue their fun with a double dong in both their pussies after the boss had finished his speech.

They were no strangers to sex – they had done 69 with each other many times since meeting the previous month, and also fucked and sucked a few guys their age. However, they were both keen to try an experienced guy and had decided that they would find a way to do a 3some with their new boss, Simon, very soon.

In the front row, Claire could hardly concentrate. Unknown to Simon, she had a crush on him and often thought about what his fat cock must feel like as she lay in her bed slowly playing with her young, wet pussy.

Unlike most of her friends, she was still a virgin. This made her miserable. She was nearly 18 and she knew that she had a hot body and she was so keen to experience real sex. She had plenty of opportunities but she didn’t want some young, selfish, inexperienced guy sticking his skinny cock inside her and cumming inside two minutes.

She looked around and saw the two bi girls in the back row. She knew what they were doing and that they had plenty of experience already. They had offered to do her several times. The prospect excited her and she knew she might say yes soon. As for guys, by contrast to the two girls, she had never even tasted sperm or even touched a cock. It was so unfair.

Her pussy was on fire and she was trying so hard not to touch it. When she saw Simon’s cock twitch, she nearly came, Her panties were soaking and she knew that she would play with her pussy in the toilets right after the lecture. She wanted to rub her clit and cum hard thinking about her boss’s cock.

Simon finished his speech and allowed them to leave. The girls left in a hurry, many of them with dripping pussies. Claire would not be the only one heading for the toilets for some sexual relief.

An hour later, Claire was about to leave the main building to go home. One of the other senior managers saw her and hurried over.

“Claire, do me a favour and take these papers over to Simon’s office before you go. He’s expecting them”

Claire nodded, not trusting herself to speak. Wow, she had an opportunity to be with Simon alone. Even though she had recently enjoyed a delicious orgasm in the toilets, she could feel her pussy was still aroused.

She walked quickly to his office at the end of the corridor, thinking naughty thoughts about what she would like to have happen. She paused outside his door and decided to be bold – she hitched up her skirt so it showed off all her long toned thighs. She wanted to see his fat cock twitch again. She giggled to herself and knocked. No answer so she knocked again. Disappointment spread across her face. She decided to open the door and leave the papers on his desk.

As she was about to leave she heard a noise and realised that Simon was in the ensuite toilet. The door was open and she could see his reflection in the mirror. She moved closer so she could see him more clearly. She gasped. Simon was masturbating his cock and, as she looked closely. She could see that it was very thick and about 8 inches long. She moaned inwardly and clutched the edge of his desk for support. Her hand slipped inside her panties and she pressed her fingers against her clit – she could not help herself, and immediately an orgasm ripped though her young body – she moaned out loud.

Simon emerged from the bathroom, his thick, erect cock swaying gently, and looked at Claire – stunned disbelief all over his face. Her face was flushed with sexual desire but he could see that she was about to dissolve in tears. He took her in his arms and held her tightly.

“Oh, I’m so sorry” she sobbed. “I fancy you so much and I want you and…and…” she started sobbing again.

Locking his office door, Simon sat on her chair and pulled Claire to sit on his knee. She buried her face in his chest as her sobbing slowly stopped. Simon had his arm around her neck and his hand covered her left breast. Gently, he massaged her breast and soon felt her young nipple hardening under his touch. His right hand caressed her upper thigh and then moved up to stroke her pussy though her sodden panties. He kissed her on her neck and softly nuzzled her ear. His cock was as hard as a rock and sticking up between her thighs.

Claire’s breathing quickened. She loved the feel of his hands on her breast and pussy and could feel her juices dribbling into her already soaked panties. Simon turned her face towards him and kissed her softly on her sweet lips. His tongue met hers, the sensation was divine and she hoped it would never end. She looked at him with her innocent eyes, full of sexual tension and expectation.

Simon eased her off his lap and lay her on the carpet in his study, putting a cushion under her head. He looked at her for a few seconds then said softly:

“Claire, this will be our secret forever, ok and….please call me Simon”

“Oh yes Boss…Sir…. I mean Simon….um…I’ve been wanting this for so long…and…um.. I want you to do everything to me and me to you”

Simon reached down and caressed her long legs from her ankles to her upper thighs. He hooked his fingers around the waistline of her juice-soaked panties and slowly eased them down. Simon lifted her short skirt and gazed in wonderment at her young shaved pussy. He was determined to give her the best oral of her young sweet life, not knowing that Claire had never experienced oral at all.

Simon bent down and slowly nibbled the inside of her thighs, allowing his tongue to leave a moist trail. He could smell the sexual aroma from Claire’s pussy and could see that she was already very aroused. Her lips were full and slightly spread. They were covered by a thin coating of sweet pussy juice that his tongue would soon savour.

Simon extended the tip of his tongue and licked her pussy lips from top to bottom and back again. Claire moaned at the sensation. It was her first experience of a tongue in her pussy and she was starting to realise what the other girls had been talking about for so long. She decided that she would soon try a few of the other girls’ tongues and compare them with Simon’s. A dribble of juice leaked from her pussy as the erotic thought washed through her mind.

Simon found her little cit and rolled it gently between his lips. Claire gasped at the sensation. She could not believe sex could be so satisfying. Slowly Simon eased a finger into her tight pussy. Suddenly, he met resistance, her hymen, and realised that Claire was a virgin after all. He groaned inwardly and his mature cock stiffened further at the prospect of taking her cherry.

Simon gently caressed her clit with his tongue, occasionally flicking the tip. Claire’s breathing was becoming more laboured. She was literally gurgling with contentment and Simon could feel spasms starting to ripple through her young body. He spread her lips wide, reached up and rolled her nipples in his fingers and then sucked gently on her clit. The effect was immediate. Claire squealed as an intense orgasm erupted in her pussy and, to Simon’s surprise, a wave of sticky cum juice flooded out of her pussy all over his tongue. The orgasm continued for many seconds – by far the most intense that Claire had ever experienced – and her pussy pulsed visibly, her tight entrance opening and closing.

Simon leaned forward and kissed her gently on the lips and she tasted her own tangy pussy juice.

“Claire darling, we will have many sessions and explore lots of things. Today, I want to do only one more thing and we can do some more tomorrow”

“Yes, Boss…I mean Simon” she replied innocently, still breathing heavily.

“Now, I want to slide my cock into your young sweet pussy and be the first guy to fuck you. Would you like that?”

“Ooooh Simon, yummy. Please fuck me with your big Boss cock. All the girls talk about it so much and I think about it all the time filling me up”

Claire lay back and spread her long thighs, looking at Simon with a mixture of nervousness and wanton desire. Simon knelt before her and held his fat cock. He slowly rubbed his bulging cock head up and down her pussy lips until it was glistening with her sticky cum juices. Slowly he pressed forward and his cock head slipped between her pussy lips with a soft plop. Claire gasped. She already felt stuffed and he was only part way in. Simon thrust with a few small strokes until his cock head was in about 2 inches, resting against her hymen.

He reached out and held her hand.

“This may hurt briefly. Then after that, we will have so much pleasure again and again”

Claire nodded nervously. She had read stories though she was resolved to get past this stage quickly.

“Do me hard” she replied “I want you to burst through”

Simon nodded and suddenly thrust forward. Claire screamed as Simon’s fat cock tore through her hymen and a dribble of blood leaked out of her pussy. He paused as his cock lay embedded deep in her pussy, and Claire gathered her senses, and then he started pumping slowly with long, deep strokes. Her face transformed as the fucking sensations began to roll through her.

“Oh yes, Simon, ooooh…fuck me, fuck me with your big Boss cock”

Simon fucked her, slowly and gently at first then harder and faster. Every time he thrust forward, Claire squealed and a trickle of juice escaped from her sore pussy. The sensations on Simon’s cock were amazing. Her pussy was so tight and it felt like her virginal muscles was pulling him in on every stroke – by far the best pussy that he had ever tasted or fucked, he thought. He was looking forward to giving her a complete sexual education…mmm

Without any bidding, Claire raised her legs and hooked them over Simon’s shoulders. Simon slammed into her, hearing the squelching sound as his cock slid all the way through her wetness each time. Claire could feel a massive orgasm building as Simon’s cock rubbed against her clit and sank into her tight pussy so deeply.

“Oh….oooh….ooooh, Simon…I’m cumming….oooooooh” she gurgled

Claire’s young body arched as she let out a long cry. A massive orgasm erupted in her young pussy and rolled through her entire body. She nearly fainted from the intensity as it went on and on.

Once again, she produced copious amounts of sticky cum juice that washed over Simon’s cock head. Simon gasped with the sensation and knew that he would shoot his load very soon. Reluctantly he started to withdraw his cock.

“No, Simon, fill me with your lovely cream” Claire pleaded and locked her legs around his back pulling him back in.

Simon was helpless in her grasp as a torrent of warm cream spurted from his cock, deep into her pussy. Again and again he spurted as he dumped the biggest load in her gorgeous hot pussy. It was by far his most powerful orgasm ever.

Finally, he pulled out breathing heavily. He looked in amazement as Claire’s pussy pulsed once again and he could see his cum slowly oozing out of her gorgeous tight hole. He could not help himself and buried his tongue in her pussy and licked out their combined cum juices. Once more, he kissed his new lover and dribbled their cum juices from his mouth into hers. Claire sucked them down greedily…mmmm

Claire lay in Simon’s arms, cuddling intimately. She had just had the best experience.

“Simon” she asked innocently “that was fantastic. What more is there to do”

He looked at her in astonishment and chuckled

“Well, at least twenty more fuck positions. Then sucking my cock and swallowing my cream, exploring your ass with my fingers, tongue and cock, perhaps some games with blindfolds and ropes, then of course sex in unusual places”

He chuckled again as he watched the astonishment grow on her face.

“I want to try it all she said hornily”

“Then, of course we might try a 3some with another girl”

Claire paused for a moment.

“Well I don’t know about a 3some but I know two girls who were there today who would love to play with you and I’ve always been keen to taste a pussy. Would a 4some be ok” she asked coyly then chuckled at the look of astonishment on Simon’s face

“Also, I have two close friends outside work who are both virgins and it would be great if we did them together”.

Claire looked at Simon’s cock that was slowly stiffening again. She reached for it and stroked it gently in her hand, feeling it transform under her touch. She leaned down and slowly took his swollen cock into her mouth and caressed the tip with her wet tongue, feeling his cock stiffening rapidly.

“Mmmmm….Simon, can we make a start on those twenty other fuck positions” she asked with an expression of naughty innocence. They both chuckled.