Category: First Time Virgin Sex Stories
Published: Nov 16, 2008
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Standing with his back to her a smile so bright lit up her face. Bare feet, jeans, and no shirt on his back he stood organizing some books on a shelf. The once affable nerdy nobody had grown and blossomed into a man. Her student in two classes in his junior and senior year, she began noticing a slow transformation none saw in him during those years.
"You've done well and I'm proud of you Jason, very proud of what you accomplished" she told him upon graduating. She looked beautiful too. He liked her very much. Never before had she looked so elegant in his opinion. "Don't forget me" she joked. "Just because you're going off to college doesn't mean I don't exist anymore."
He said he wouldn't. They embraced, so she patted his shoulder, and dearly wanted to kiss his cheek knowing it would be inappropriate. She turned and walked away, with her fiancee. He knew nothing of the guy, but it wasn't his business; never was. Still she thought about Jason. Thought about him excessively, hence her engagement was off. She had to start over. Another man, another long, long relationship, and then another long engagement period... "Fuck that" she felt like saying. She devoted herself to her teaching.
6 months later, it was a holiday break, and what did he do Jason visited his high school seeking out Olivia Henson, his former teacher; his favorite teacher. She always sent unknown emotions threw him. He figured it was puppy love. His dad told him all boys have it in their lifetime so he guessed that's what he felt for her. They met up, they talked, and they laughed about many things. They said goodbye, but for whatever reason it hurt having to leave. They'd get together, after school, but it never once materialized.
He came to see her that spring, but she was unavailable. Time passed, things changed, but his feelings for her hadn't. No, no they hadn't. They only matured. 4 years later, he was a college graduate. He had taken up an exercise program, lifting weights, and running some and he looked every bit the man. Sculpted, broader shoulders, and a couple inches taller Jason was a stud and he didn't mind walking around in certain places without a shirt on. Proud of his newborn physique he couldn't wait to see her. She had lost some weight too, but regardless he was fond of her, but she was in for a big surprise once she saw his newly remodeled frame.
Her jaw would drop, but his might too. Right out of college, he got a job. Right out of college, he invited her over. Right out of college they were going to hit it off.
"It's about time" she said from the front door. Then she saw his body. "Jason... Jason is that you" He turned slowly. A smile garnered his face. Pecs, tight stomach, and in sexy jeans with no shoes on and Jason looked perfect in his beach house setting. She couldn't believe her eyes. Hearing the wave's crash the beach as he turned to see her reaction, Olivia couldn't believe how much he had changed, physically. "Jason, wow Jason you have... you have" but her eyes said it best. They were all over him and telling him how she appreciated his physique. He was delighted once he saw her response. "You've changed, Jason."
He walked to the door, invited her inside, and before she could say anything or he could too, he embraced her again. Her nipples surged. Her body swelled excitedly. She couldn't believe how his newly developed frame aroused her the way it had. He was 22, she was 31, but it no longer mattered because her former student was a man now and he showed it in every way. She had changed. She had lost weight for her wedding. But seeing as the wedding was called off several months ago, she was still sexy. She was still pretty as ever. He told her so. She felt like it too in his arms. He really didn't want to let go of her. She didn't mind him holding her as long as he did.
"That's a rather warm welcome" she said teasing him.
"Oh uhh I'm sorry... I didn't realize I was being so boorish. It wasn't, she was only teasing, but that was still one area he hadn't "grasped" quite yet. Social graces, he was still clumsy as ever, but as handsome as he had grown, physically sexy too she didn't mind. She didn't mind the least bit. His arms, they felt incredible around her. His newly "minted" masculinity wrapping itself around her newly "redeveloped" figure just seemed to fit, for whatever reason, perfectly. He pulled away, letting go of her, and told her "I don't... I don't know what got into me Ms. Henson."
"Nothing got into you, Jason. It was a normal, everyday reaction" she said.
That day at his beach house as the sun began warming up to air, she had decided to put on that off white frilly skirt. Light weight, it blew every which way in a breeze. It moved everywhere and if there was an up breeze, sometimes she had to do everything in her power to push it down making sure nothing private was exposed. This was one of those days. With that lightweight frilly skirt she wore that sleeveless print blouse. They went together impeccably. She put on several outfits but after trying on about seven, she finally decided on that one.
"Nothing got into you at all. It seemed like the natural thing to do. Hug someone you care for, maybe hug that person longer then you expect, and well there isn't anything at all wrong with it. Now are you going to show me around, off her me a drink"
She hoped they'd go swimming. She brought her bikini, she brought changes of clothes. She wasn't sure what might transpire, but she hoped something might. Geeky or not it was a chance for that woman to upgrade her sexual escapades again. It had been a while. She knew that for sure. Urges had been knocking, no banging hard at her door, and she needed to upgrade and pacify her overwhelming urges which bothered her lately.
Regardless if he did look different he still felt like the same old nerd, same old geek he once was in high school, especially with her around, but she did that to him. She had that affect on him. He didn't mind. He liked her. Plus, she looked prettier then ever, lately. He gave her a tour, even showed her his bedroom and master bathroom. He showed her the community pool and even asked her if she brought a bathing suit, hoping it would be a bikini. She had, but didn't say it was a bikini.
He even offered her wine. She accepted. The day was getting better, slowly. The temperature had risen. It was 90 degrees, humid, and it was time for a nice swim down by the beach. His was a rented property, isolated too, and he was proud of his negotiating in securing the place. He told her how he negotiated it. She was impressed. He went and put on trunks and they walked down to the beach, but she still hadn't put on any bathing suit. He asked if she wanted to go swimming. She said later.
He swam, they talked, and she sat admiring him. As they talked and as she sat admiring him those urges grew. They grew immensely. She asked to go inside. He said yes and they did. Inside it all changed. Everything changed.
"I can't get over how much you've changed, Jason."
He wasn't sure what she meant. She told him, but not the important things. She truly desired her host. He sat wrapped in a towel around his waist, chest protruding and teasing her, as her heart and vagina thumped harder and harder by the moment. They talked more. They started talking about feelings. His feelings, some of her feelings, but she couldn't hold out.
"Jason...I must tell you something." She stood. He sat back not understanding her. "This probably isn't a good thing, but... but I think I'm becoming... I think I'm attracted to you." His eyes popped from their sockets. He sat upright. She turned to look directly at him. She wasn't smiling, but she was concerned how he would take her remark. She hoped his response was promising. It seemed to be, but she wasn't sure. She could tell he was shocked. "Jason... Jason" she said.
He was still stunned. Yes, he had thoughts about her like that, occasionally. Yes, he had wondered about her and him on dates. But no, no he hadn't ever once thought of her in a sexual sense of the word. Dinner and clubbing, yes, but sex not that he could recall.
She decided to make a move, see what happens, so she stepped closer, slowly coming towards him. Running her hand over his shoulder, around the back of her neck, and across the other shoulder too suddenly he tensed up. She could feel his body tighten. She asked him if he was okay. He said yes, nervously, but it didn't sound reassuring. No she was sure of that, but she persisted. She needed a man's touch regardless if he was experienced. She wanted a man's body, regardless of his experience. She always liked Jason and she knew Jason always admired her, but now there was something different something different in the way each communicated. She was anxious, but not nervous. She was aroused by his good looks. She anticipated the possibilities and had to relax the former student, somehow.
Suggesting they go to the balcony, he agreed wholeheartedly. He hopped up immediately and they stood out there looking at the water. The breeze was warm and comforting, but it periodically kicked up and thrashed her skirt around. He'd look and see it blow here and there, but he hadn't caught it yet flying all the way up.
She pushed it down too many times and finally he realized it. He watched and he paid attention and finally that damn breeze got his approval. It blew her skirt upwards, blowing it all the way up. What the hell What the heck is she wearing Was that a g-string bikini or was it simply bikini underwear Blow... blow harder wind, blow harder.
"Do you like that" she asked finally.
"Huh, pardon me" he replied.
"When my skirt... when it flies up like that"
"What... I'm sorry" he began "I'm not sure what you mean."
She smiled. She said yes he did. He behaved innocently. He knew. She knew he knew. Yes, she had put on bikini briefs. They felt sexy, they were sexy, and she had been hoping for something, anything to happen between them.
"Why don't I" but she didn't.
She wanted to take it off. She wanted to entice him. Instead she did something else. He hadn't seen her ass. He hadn't even imagined it. No, it wasn't tight like an 18 or 19 year old college coed's ass, but if he had seen it he would have enjoyed it, she hoped. Instead she unbuttoned two, then three of her top buttons. What was she doing He saw the cleavage.
God, it was sweet. He felt tingling in the tip of his penis. As soon as he felt the tingling, he could feel something changing. Something was changing. It was an odd feeling. His penis had stiffened. He was scared, he was excited, and he liked how it felt but he didn't. He felt like he should shift it around. He couldn't, not now he couldn't, and so he lived with it.
"Do you like my boobs, Jason or should I say my cleavage" she said. She smiled. "I'd like to show you more. Would you like that, Jason" He nodded. It was instinctive. Anyone would have done the same. "That's great" she said. Her voice was quiet. It was calm too. "Mmmmm, I'm glad you wanted me too. I want to show you the rest of my cleavage, my boobs too."
He stood, frozen, gazing upon it. He didn't move a muscle. He couldn't. He was overwhelmed by their beauty. She said nothing. She unbuttoned another one. She pulled her sleeveless top apart, but only a little. He felt like his tongue had slipped out of his mouth, dragging on the floor, but it was his imagination. She undid two more; one left. She undid the last one. The blouse covered it up. She watched his reactions closely. She smiled while appreciating his admiration for her sumptuous, mature nature.
"I seem to meet your approval do I" He nodded. "Good, then feel me, push my blouse back, and feel them all you care too. Be nice and be a gentleman though. I'd love it if you'd kiss them and lick them too at some point" she told him.
"What the... what the fuck" he asked himself.
Yes, Jason had seen girls in their exercise outfits and yes, he had seen them in those sport bras. He had seen some in those, what did they call them, Lycra bras or something like that Yes, they were a bit revealing and yes, he would stare, but as little as possible. He knew it was rude and he understood he was a geek. He knew how others saw him, but as always, he had persisted. He had persisted on working out, looking more buff, and girls began paying more attention, but it had been too late for anything to transpire. By the time he was about to graduate, he had seen all the cleavage or almost all the cleavage he wanted in college. But it had become too late for any of them to challenge each other to ask him out. It had become too late for him to ask them out, so one thing was for sure by the time he had graduated.
Jason was still a virgin. He had seen cleavage, but never in this situation.
"Don't you like my body, Jason" He said nothing. He ogled her. "Jason... Are you alright, honey"
Her voice... her voice was different. It sounded like honey, like sweet syrup. Her eyes, they were just like soft rain drops in the summer. That look in her eyes, that look on her face both mesmerized him, both melted away any preconceived notions he had about girls. Well he didn't have any other then most were pretty, most were sexy, and most never approached him for a date and definitely sex.
She felt like she had to guide his hand, raise it up, and she felt like she had to lift his hand up against her bosoms. Touch her soft descending flesh which fell inward into her tight looking, sexier then sexy valley. She watched his eyes, she watched his face. He stood frozen, almost frightened, and fearful of doing anything to her. He wouldn't allow himself to do more then what she allowed. He watched his fingers feel it, feel them. It was riveting. He watched his fingers descend, rolling downward along that tumbling gentle skin surrounding her breasts, and then he watched her raise them to the top again.
"Ohhhhhhh god" he moaned. His eyes closed. His penis hardened. His penis hardened and it tingled, excessively. "Oh... oh... ohhh god, ohhh my god" he cried out. She loved every bit of it. She enjoyed him expressing his every emotion. He was exciting her too.
He was a virgin. It was her first time with one too since she was young and everyone's a virgin at one point in their lives, but at 22 that was unusual, but for Olivia it was exciting as anything she could remember. He was wonderful, sweet, and a loveable guy. This was going to be fun one way or another and she knew that.
"Jason, honey, may I ask you something" He nodded. She held his hands in hers. "Is this your first time with a woman this way" She waited. He didn't want to tell her, but it was. He looked down. He nodded. "It's alright. It only makes it more... more special, more unique for you, and for me. Would you like to kiss them" referring to her tits "or just keep feeling them" she asked.
He said feel them. He didn't know what he wanted. She ran the show. She guided them, upwards, and let his fingertips roll across her lofty flesh and cleavage. Both closed their eyes. It was special for both. Both murmured, both indulged in feelings they received as his fingers felt her cleavage.
"Down... down in between them, slowly alright honey" she told him. He nodded.
She let go of his hands. They dropped to his sides. She lifted hers up and she traced lines across his pectorals. She murmured sweet nothings as she appreciated the newly defined chest muscles. She told him they were to be admired. She said she was in awe of him, his handsome body, and she wanted to know how he was still a virgin. God how was it possible that he was still a virgin He was too god damn exciting and sexy to be one.
He knew she had to know. He was so horny. But he didn't want to tell her. It was too overwhelming. He had to tell her he thought. She was trailing those sexy fingernails across his chest, tantalizing him while enjoying his sudden gorgeous masculinity. He felt like she should tell her. It was driving him crazy.
"Ms. Henson" he began to say. "Ummm well... oh god Ms. Henson" he tried saying. He was moaning again. She looked into his eyes. Putting a finger to his lips she tried calming him. She told him he should always call her Olivia from that point on. "I think I'm... well I am... I'm horny, Olivia. I feel like... I feel like I'm, well I don't know how to tell you, but I feel like" but she knew. She knew by the look on his face and she told him.
Whispering practically she said "You are horny aren't you You feel so horny that you feel like something is going to explode inside. Your penis, your cock... it's harder then you've ever imagined it to be, right" He could barely nod his head. She smiled, kissed his cheek, and kissed his lips. "I'm going to make this all better now."
She lowered her hand, slowly. She lowered it down, carefully. She caressed his tummy. He groaned in a silent manner. She leaned in and kissed his lips. She lowered her hand over his waistband. She lowered it over his zipper line. He tensed up. She slowed and cross over his bulge, slowing more while crossing over it. She pressed, firmly, as she crossed over it. Olivia drew so much excitement she moaned. Her eyes closed, her hand stopped, and she pressed harder and harder against his erection.
"I want... Jason I want to see it" she said. He didn't understand. She blinked and smiled. "May I see it May I see your... your penis, your cock please" He was freaking out. He nodded and pushed down his jeans. There it sat. Pulsating, tingling excessively, and barely enabling him to do anything. He stood frozen in his underwear looking at her and wondering what she was going to do. She no longer was Ms. Olivia Henson, his teacher. That was 4 years ago. Now she was simply a woman, a horny woman who used to be his teacher who wanted him for sex, but wanted also to be his friend and lover, part time or not, but a willing and participating sex partner.
"Mmmmmm Jason oh Jason ohhhhhhh wow Jason" she moaned "it's so beautiful, so manly, and I'm so lucky to be with you today. I'm so, so lucky to bring you something I'm proud to give you. You're a man, Jason... a real man."
And she dropped to her knees and Jason at first had no idea what she was doing but she reached in, pulled it out, and she gripped it with the palm of her hand, and she immediately swallowed his cock. She swallowed him whole. His knees went weak. His body was fragile. Her mouth sucked on his cock so hard that before she realized anything Jason was unloading himself inside her. Jason was unloading it inside her petite mouth. She gagged. His cum came strewing out. Oozing down each side of it while still unleashing pent up loads never once unleashed on a woman before. Never before had Jason felt the luster of a woman's lips or tongue. Never before had he felt the beauty of a woman sucking and swallowing his cock, energizing it, and stimulating him I ways he never could imagine he thought, but Olivia had. Olivia was immaculate. She teased and tantalized him and she was beautiful. She was older and seductive and she was perfect in her execution of his first ever blow job.
But there would be more.
"Wow Jason wow" she said looking up at him with bright eyes. She was smiling. Jason was too. "If I hang out today will you do me a favor"
"Anything you want Olivia" he told her.
"Will you have sex with me I'd love that more then anything today."
Jason nodded, smiled, and got down on his knees. He hugged her, hugged her breasts, and told her he wasn't letting go of her until she would. She said it was a deal. She kissed him, they lay on the carpet, and within two hours, she was on top screaming like she hadn't screamed in ages, which she hadn't.
"Mmmmmm you sure are sexy, Olivia. God if that's how fucking you is... then I'd fuck you the rest of my life."
"It is and you were awesome too" she told him. "And you're no longer a virgin either."
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