Sex Ed 101

Julia looked at the young man in front of her and thought again how sad he was. Robbie and his parents had lived next door to Julia for many years, and Julia had been his babysitter and then became his friend as Robbie grew older. Through the years, Robbie had confided in Julia, and Julia knew that Robbie’s lack of ability with girls, women now, was a source of great disappointment and sadness for Robbie.

While Robbie was in high school, he would excitedly tell Julia about an upcoming date, usually a blind date, but then would tell Julia afterwards that it did not go well. Julia had tried to comfort him through the years by telling him that thing would change.

Robbie was now 19 and had just returned from his first year of college. He was telling Julia that his luck with women had not changed. Friends had set up dates for him, but he would sense during the evening that his date was not having a good time, and on several occasions, girls found excuses to leave him without him. Robbie said “I think I’m the only male virgin on the campus. I’m not only a virgin, but I’ve never touched a woman’s breast or kissed a woman passionately”, and Julia thought she could see tears in his eyes.

They visited some more, and as Robbie got up to go back to his house, Julia told him that it was wonderful to see him, and again told him that things would change with women.

After Robbie left, Julia thought about her young friend. Julia understood why women did not find Robbie interesting. He was the classic nerd, tall and thin with thick glasses and with a complete absence of social ease. Julia thought “if they only knew how sweet he is”, but then realized with a smile that that was the classic thought by a friend about someone not appreciated by the opposite sex.

Julia and her ex husband had bought the house in which Julia now lived about the time Robbie’s parents bought their house. Robbie was a toddler at the time. Julia’s husband left her not long after. Robbie’s Mother became Julia’s closest friend and was the one who helped Julia survive the emotional turmoil of her marriage breakup. Robbie’s Dad, Jim, had been a Godsend too, often helping Julia with tasks meant for a man. Julia knew that Jim found her attractive, but he had never made a pass at her which caused Julia to think even the more of him.

Julia was now 43 and still single, although she had had plenty of suitors since the day her husband had left her. Julia was tall and slim, and she still wore a four dress size, the same size she wore when she graduated from high school. Her blonde hair and sea blue eyes made her even more appealing to men.

While Julia would not sleep with every man she dated, she would do so if she liked the guy. So, sex outside of marriage was not a stranger to her.

She thought more about Robbie. “Poor guy” she thought. She did not know any women Robbie’s age, but wondered whether any of the other women in the law office where she worked as a Legal Assistant might know any women Robbie’s age. “But”, she thought, “without some changes in Robbie, the result of any date I could find for him would likely the same.”

Julia continue to consider what she could do to improve his ability with women. She had talked to him many times, trying to encourage him to be more confident and relaxed around women, but while Robbie listened to her, he could not easily alter his personality. So, it occurred to Julia that there was little she could do.

The thought then hit her that the one thing she could do was remedy his status as a virgin. She giggled as she contemplated that, thinking that that would be a very large contribution to a friend. But, she thought, why not? She was an adult and so was he. Having sex with a man with whom she had not had sex before was no big thing to her. She wondered about his parents; would it destroy their friendship if they found out? She concluded that Robbie’s parents would be so grateful to her that it would further cement their friendship rather than harm it.

She was still thinking about it when she saw Robbie’s parents pull out of their driveway, obviously going out for the evening. She picked up the phone and dialed Robbie’s house. Robbie answered.

“Hi Rob, this is Julia”

“Hi Julia” he responded, a bit of puzzlement in his voice at hearing her on the phone.

“Rob, I just saw your parents leave. Are you home alone?”

“Yes, I’m here alone as usual. You are not going out tonight?”

“No, I’m staying home tonight, but I would like some company. Why don’t you come back over and visit with me?”

“Ok, sounds good to me. Are we going to watch a movie or tv?”

“No, Rob, I’m going to give you sex ed 101.

There was silence on the phone. Then Julia could hear Rob trying to clear his throat. Finally he said “I must not have heard that right.”

Julia responded “come over about eight”, and she hung up the phone.

Julia giggled to herself as she thought about what must be going through Robbie’s mind. “He probably didn’t take me seriously” she thought “but he is going to be in for a very pleasant surprise.”

Julia showered and carefully shaved her public hair. She normally kept it closely trimmed, but decided that she wanted the first pussy Robbie would see to be clean shaven. She rummaged through her closet and found the sexiest clothes she could find. She started with her usual white bikini panties but matched them with a sheer bra. She wore a very light sweater shirt, one which was so light that her nipples would show and which was cut low enough to show a lot of her D cup breasts. For a skirt, she put on the shortest skirt she had which accented her long, slim legs. She really had to dig deep in her closet, but she found the “fuck me” heels that she had worn only a few times.

She was just finishing her make up when the door bell rang. She opened it and Robbie stood there . . . and stood there . . . making no effort to come in. He was uptight Julia could see. She idly wondered if he would be able to get it up he was so uptight. He finally managed to say “these are for you” and held out a dozen roses he had been holding behind his back.

“Oh, they are so pretty Robbie . . . that was so sweet . . thank you . . . please come on in.”

“Have a seat in the den Robbie. I am going to put these pretty roses in a vase and pour us some wine.”

When Julia returned, Robbie was perched uncomfortably on the edge of her sofa. “Poor boy” she thought “he’s petrified”.

Robbie had sat at the end of the couch and Julia sat with her legs touching his. “Let’s sip on our wine and visit Robbie” and the two of them did. Julia thought Robbie began to relax a bit as he downed the wine. She leaned forward toward him as they chatted, letting her sweater fall away from her body. At first, he avoided looking, but as the wine took hold, she noticed his eyes becoming more adventuresome.

After they had finished the wine, Julia took both glasses and put them on the coffee table. She returned to the couch and sat next to Robbie folding her legs up under her which caused her skirt to ride up very high on her thighs. She looked him in the eyes, still seeing a very nervous young man. She leaned forward and kissed him lightly on the cheek. As she did, she removed his glasses and put them on the coffee table. She kissed him again, letting her lips linger on his cheek. She continued to kiss his cheek, moving her lips around, giving him sweet little kisses.

She reached his lips and kissed them lightly, just brushing them with her own. “He has very soft lips” she thought, “kissing him will be a pleasure.”

She took his face in her hands and turned it to her, and she kissed him more passionately on his lips, brushing her lips over his in all directions and then pressing harder into his lips. She continued to kiss him, on his lips and then sweet kisses around his face, but always returning to his lips. Then she kissed him hard on his lips and pressed her tongue against his lips. She felt him move, surprised at her tongue. But he parted his lips and she slipped her tongue into his mouth.

She continued to french kiss him, moving her tongue in and out of his mouth, caressing his lips and his tongue with hers. She felt him began to respond with his tongue, although tentatively. Then Julia felt Robbie reach out and touch her breast. Julia caught herself just before she giggled, thinking Robbie was just like the character in The Graduate. She smiled at him to let him know that it was ok. He kept his hand on her breast, but clearly did not know what to do with it. Julia continued to kiss Robbie and he responded with stronger and stronger kisses. “Well, he’s getting the idea about kissing” Julia thought. But the hand just remained resting on her breast. “Mmmmmm Robbie, you kiss very nicely. I like that” she told him. She heard Robbie mumble something that sounded like “thank you”.

Julia decided that it was show time. She broke their embrace and said “Robbie, why don’t you unbutton my sweater.

His hands, shaking, went to the top button on her sweater. It took him a while but he got the first button undone. The second and subsequent buttons went much more quickly.

Julia pulled the sweater open and watched his face as her breasts came into view. His eyes looked as if they were going to pop out. “Like them Robbie?” she said. He nodded his head, saying nothing, but not taking his eyes off her breasts.

Julia reached behind her and unhooked her bra. She slowly let it fall off her breasts as Robbie watched intently. His eyes got even bigger as her nipples came into view.

After she had dropped her bra to the floor, Julia said “Robbie, why don’t you touch them again,” and Robbie’s hand went immediately to her breast. His touch on her naked nipple startled her a bit, and she said quietly “ooooooooohhhhh”. Robbie took that as a sign she was enjoying his touch, and he became more aggressive with her breast, cupping it first and then taking her nipple with two fingers. She let him continue, although he was applying so much pressure he was hurting her a bit. “Best not to discourage him” she thought.

After Robbie had enjoyed her breasts for a time, Julia decided it was time to move on. She smiled at him, and stood up and turned around with her back to him. She unzipped her skirt and slowly slipped it down her legs. She kicked the skirt away and turned to face Robbie. His eyes were right where she thought they would be - her crotch. She let him look and turned slowly letting him look at her ass.

She stopped her turn in front of him and said “Stand up Robbie”. He looked puzzled but stood up as ordered. As he stood, Julia noticed the bulge in his pants, thinking not only that he was working just fine, but that that was a very large bulge.

Julia kneeled in front of Robbie. She looked up at him and smiled and reached for his belt, unbuckling it. She pulled the belt out and tossed it aside. Continuing to look at Robbie, she unzipped his pants and pulled them down his legs. As his slacks passed over his cock, she thought “My, he is very big, but why does he wear jockey shorts. Yuk.” She helped him out of his slacks, and she looked at the bulge in his jockey shorts.

“My, Robbie, you are huge.” She heard only a gurgling sound from Robbie as she put her hand on that bulge, caressing it. She then took the hem of his shorts and worked them downward and over his cock. It sprang free, and he was huge. Not particularly long, but incredibly wide and thick. She looked at it and then looked up at Robbie. She moved her face to it and then licked the head of his cock and then ran her tongue all around its head. She looked up at Rob again and saw what she knew was raging passion on his face. She took his cock and leaned forward again, taking it into her mouth. She took it as deep as she could, sucking on it, and then letting it slide out of her mouth slowly. With her hand, she cupped his balls as she took his cock in her mouth again. He was hard as a rock and he was beginning to hump, and Julia was afraid he was close to an orgasm. She didn’t want it to end there, so she slipped his cock out of her mouth and stood up.

Julia took his hand and led him to her bedroom, slipping off her panties as she went. She had placed a tube of KY beside the bed and she quickly squeezed some out of the tube and rubbed it on his cock. She then climbed on the bed and place a pillow under the small of her back. She looked at Robbie and said “ fuck me Robbie.”

Robbie climbed up on the bed between her legs, clearly not certain what to do. Julia leaned up and took his cock in her hand and guided it to her pussy. She found the opening and placed the head of his cock there. Instinct took over then as Robbie let his weight fall onto her which drove his cock into her pussy. Instinct continued to work for Robbie as he began to hump Julia. Julia was enjoying having his very thick cock in her, and she tried to hump with him, but his weight made it hard for her to move. She knew he would not last long.

Robbie’s humping picked up the pace and he was really pounding Julia into the bed. She felt his cock swell in her and then he began to growl like some wild animal and Julia knew he was cumming. He pounded her and growled and shook as his orgasm went through his body. Julia wasn’t counting, but his orgasm seemed to last forever.

Finally, his movement slowed and he collapsed on top of Julia. Julia could feel his cum running out of her pussy and between the cracks of her ass. She wondered what to say next and decided on “Robbie, that was very good.”

He raised up and smiled at her and said “thanks”. He clearly did not know what to do next, but Julia rescued him by curling up in a ball and pulling him around her spoon like. Neither said anything. Julia was thinking she had really taken one for the team, but then remembered that while it did not last long enough for her to have an orgasm, it was good.

As they lay there, Julia felt movement against her ass. “Oh no” she thought, “he’s getting hard again.” Sure enough she soon felt his big cock, again engorged with blood, between her legs. “Can we do it again Julia?” All the guys I know talk about how great doing it doggie style is. Can we do that?”

“Oh my” thought Julia, “I didn’t even do that for my husband when I was married without a couple of glasses of wine.”

But she said “sure, we can do that.” Julia got on her hands and knees with her head on the bed. She felt Robbie getting behind her and his cock on her ass, but again he seemed unsure where to go with it, so she reached behind her, took it in her hand, and guided it to the lips of her pussy. Robbie felt the slight insertion and pushed it in the rest of the way and began to hump her from behind. As she took her hand away from his cock, her hand brushed her clit, and it hit Julia that she could stimulate herself from this position.

So while Robbie fucked her from behind, Julia worked on her clit. The entire evening had been sensuous to her, from the thought of seducing this young man, through the first time he fucked her. It did not take long, and Julia found herself on the verge of an orgasm. She said “Oh fuck, I’m coming!” and began to hump on Robbie’s cock in earnest. Her pussy squeezed Robbie’s cock as she went into her orgasm and that sent him over the edge, growling again and pounding her from behind. His assault prolonged Julia’s orgasm and she squealed and shrieked as she shook from her orgasm

As their orgasms waned, Julia collapsed onto the bed and Robbie on top of her. They lay there. Julia managed to turn her head toward him and say “Robbie, that was very, very good. I had an orgasm and that is very rare for me with intercourse. You have a right to be very pleased with yourself.” She saw Robbie smile and that smile told Julia that she had done well that night.

Robbie climbed off of her and off the bed. “That was great Julia” he said, as if he said that to all his conquests. “I’m going home now.” As he walked out of her bedroom, he stopped and picked up her panties where she had dropped them.

“I’m going to keep these as a souvenir. All the guys at school do that.” And with that he left.

The next morning, Julia was working in her kitchen when she saw Robbie in his driveway. He was standing straight talking to a neighbor, reflecting in his body language a level of confidence Julia had never seen in him. Julia smiled.