“No, I would love it,” Jim said, a little too eager. He felt his face flush again. Then his eyes grew wide as she watched Jenny turn and stretch to place her coffee cup on the coffee table behind her. As she reached back, her legs parted, giving Jim a perfect view directly up her dress. He almost let out a moan as he saw her smooth thighs above her thigh high nylons and the silky crotch of her pink panties. She seemed to take a long time placing the cup on the table before she turned back to Jim. It spite of himself, Jim felt himself getting hard as he saw her legs stay wider then was ladylike.
The two talked for a while longer before Jenny said, “Well, I guess I had better get back downstairs or my supervisor, ‘Mildred the terrible’, will have a cow.”
“Oh, I hear she can be a shrew,” Jim laughed. “Uh…uh…would you, that is if you don’t have plans, like to…uh you know…go to…” Jim stuttered.
“Go to lunch? I’d love to,” Jenny said finishing Jim’s sentence for him.
“Oh great, I’ll stop down at noon,” Jim said excitedly.
“Wonderful, I look forward to it,” Jenny said, her smile lighting up the room.
Jim and Jenny went to lunch that day and three more times before Jim got up the nerve to ask her out. He was very disappointed when she said that she would have to think about that. Then he chastised himself for ever thinking that a young beautiful girl like her would ever want to go out with a 38 year old man.
Jenny just needed a little time to think. She was growing to like Jim. However, there were a lot of reasons why she should say no. He was sweet and handsome but too old for her. Besides, it is rarely a good idea to start a relationship with someone that you work with. Then Jenny thought, what the heck, it is only a dinner, she could control things.
Jim was ecstatic when Jenny called the next day and accepted his offer. He was walking on clouds the rest of the week. As Friday neared, he became more nervous. However, the date went wonderfully. Jenny made him feel very comfortable and really acted like she was interested in what he had to say. When the date ended, Jim was not presumptuous enough to kiss her good night, no matter how much he longed to do it.
Jenny thought Jim was so sweet. He put no pressure on her to take the relationship further. That was a refreshing change from her normal dates. She decided that she liked him a lot.
On the third date, Jim stood outside Jenny’s apartment saying good night. He was unusually nervous. Finally, he blurted out, “Do you mind if I…if I…uh, kiss you good night?” he asked with a red face.
“Of course you can kiss me, I thought you would never ask,” Jenny said, her eyes sparkling.
Jim sighed in relief and took her into his arms. His head was spinning as he smelled her perfume and held her soft body close to him. He could feel her soft breasts pressing to his chest as his lips met hers. Jim was a little surprised when Jenny pressed her tongue into his mouth. He moaned quietly and began to suck. When Jim pushed his tongue into her mouth, Jenny opened wide and accepted it, sucking hard. Suddenly Jim was mortified when he felt his cock begin to harden in his pants. He thought about pulling his hips from her to hide his excitement. But he was relieved when Jenny pressed her body tightly to him, squeezing his now hard cock to her stomach.
Jenny moaned in spite of herself when she felt Jim getting hard. She was in an emotional turmoil. Normally she would pull her date into her room and fuck his brains out. She knew that Jim was different; she knew that he needed time to get used to a relationship with a woman again. Besides, she was not sure of her own emotions. They had already gone far beyond where she originally felt comfortable. However, there was something about Jim that drew her to him. In could be that he was such a gentleman and was so different from the pawing she typically got from her dates. Not that pawing was bad she thought. It was just nice not to have to be pressured to go to bed with someone.
When Jim pulled away, his breathing was a little heavier, his cock throbbing like some teenager on his first date. He hoped that Jenny didn’t look down; she would surely see the wet spot on his pants.
The truth was, Jenny’s panties were wet as well.
Over the next month, Jenny and Jim dated several more times, each time Jim kissed her at the front door. Jim wanted to go further but was afraid of the rejection.
Jenny was unsure where she wanted the relationship to go. She felt sexual excitement with Jim but she had her other lovers and she felt free to be as sluttish as she wanted with them. She wasn’t sure how Jim would react if she knew the real wanton slut inside her. Jenny was not ready to give up those lovers under any circumstances.
Jenny didn’t want to be cruel to Jim. She knew that he needed some relief, she just wasn’t sure what that meant or how far to go. With her regular boyfriends there was never any question. Maybe a little petting would be okay with him she thought. But she wasn’t sure when or how to initiate it without scaring Jim off. Then she got an opportunity that she was looking for when Katie, her roommate, suggested a double date.
Katie was a pretty brunette who had been Jenny’s sorority sister and roommate through college. When they graduated they decided to rent a house together and share the expenses. Katie was dating an older man and seemed to prefer them. She and her boyfriend Jerry were sexually active and would often go to her room and make love through the night.
Jenny didn’t think that she liked Jerry. He had been married when Katie and he met. Jenny didn’t want to be judgmental but she wasn’t sure what Jerry’s intentions were. There was just something about him that didn’t sit right with her.