As 30 loomed close, Nan began paying more attention to where her life was going. For too many years she lived a life of little responsibility, working jobs that paid enough to get by and she could just forget when she wasn’t there. She’d watch TV, read, party, and mostly do things to keep herself entertained. That went for the men in her life to, a series of dead-end boyfriends who provided a diet of vanilla sex when she got horny.
When a girlfriend suggested checking out some of the skilled trades that could be learned at the community college on a part-time basis and would pay well after only two years, she looked into it and discovered one that appealed to her. Her budget was tighter with the school expenses now.
She moved to a rooming house to save money and there she got another idea. When the current boyfriend bit the dust, she knew older guys had more money and were always interested in younger women. She was reasonably attractive with short dark hair and c-boobs on her chest so she began flirting, seeking invitations from some of the other single male residents to take her out to dinner, one of her bigger expenses.
In the beginning that was an easy price to pay for her company but after a bit she got horny so a few times a week she offered her body for dessert. That took care of two needs at once, she figured. When she got acquainted with some nontraditional students at the college she added a couple more dinners and dicks to her list.
It was getting pretty interesting, she thought, especially with the things that these experienced men showed her in the sack, and elsewhere for variety. She had so much fun with fooling around before intercourse. Playing with and sucking and teasing their peckers made her laugh while what they did with their fingers and mouths in her crotch sometimes tickled but most of the times got her hot or got her off. Some of these older guys to be really playful and that made it so much fun. They helped her to learn not to take sex too seriously, that fucking should be just plain fun most of the time even though sometimes for sharing serious feelings. But not with them.
Soon every evening but Sunday was filled and she kept that to herself because she needed to work on her studies for Monday. Some weekends and on the vacations she could manage, these men with resources took her interesting places and they got more than just a bonking after dinner. She was getting tastes of the good life, good food, good company, and good fucking.
Some of these guys got serious, wanting to keep her all to themselves and making some damned enticing offers but she told one and all that she had to reach her career goal before she would make any commitments beyond the temporary ones she was enjoying now. Sex was much more interesting with the variety than it ever had been when she was screwing only one guy for a period of time.
Six months before the end of her schooling, she also got concerned about her spiritual development and found a church she could relate to. There were interesting talks, discussion groups, and social events but none of the guys she was fucking wanted anything to do with religion. That left the door open for Trent, a ministerial school intern who was five years younger than her. They got into some great discussions on Sunday and he said he’d like to follow up on them with dinner. The first time that happened, she wondered if she should repay him with her pussy like her other guys. She was really warming up to him and when that happened she also like to have skin on skin but was very concerned that he would judge her a “loose woman”. It seemed best to play the role of a virtuous person.
He seemed to be unusually shy and most guys would be at least trying to cop a feel or give her a tongue kiss in the hopes of loosening her up by now. It was getting a bit frustrating, considering how much she liked intimacy and entered into it rather easily.
She only saw him on Sundays because he was quite busy with his work just like she was with work and school and fuck buddies. She did look forward to their time and finally had to ask, “Trent, do you like girls?” When he said he did she asked, “I’m a girl so what do you think of me? I mean as more than just a dinner and conversational partner.”
Trent stuttered a bit and admitted he had little experience with women, but he was not gay. He thought she was a very attractive person and then added as a woman too. Nan leaned over and gave him a kiss, and then another one and then an even deeper one. He seemed paralyzed so she put his arms around her and put her chest up against him.
When she pulled back his face was flushed and he was quivering with tension. “Okay, it’s your turn to show me some affection, that is if you want any in return.” He gathered some gumption and started making out with her. After a while she took one of his hands and placed it on her breast outside her clothing. She had to hold it there so he knew that was alright, but his kisses got a bit hotter.
She whispered in his ear, “I really like you a lot and I want us to be close. I’m not a virgin and I’d be happy to feel all of you skin on skin.” She waited for his response.
He was still quite red and flustered, “I’ve hardly ever done sex so I might disappoint you.”
Taking his hands she stared into his eyes, “This isn’t a competition or contest. I will accept you as you are and enjoy what you give me. I offer myself in exchange.”
Reassured, he didn’t resist as she led him to her bedroom and undressed him, then guided him to take her clothes off. Not wanting to spook him with too much too fast, she didn’t kneel down and suck him. No need, he was as hard as could be. She laid him down on the bed on his side and got in next to him holding him close and feeling his erection between their bellies.
She began kissing him again and after a bit pulled his head down to her breasts and gently told him what she wanted. When her hand found his throbbing shaft, she barely touched when it exploded. Knowing he would be embarrassed she said, “My, you must really think I’m attractive. That was quite a compliment, you know. Let me clean it up a little bit and will keep going. I’m sure it will show how much it likes me again in just a little bit.”
It didn’t soften much, she noticed and she kept encouraging him to explore her body. Her own desire kept building and finally she rolled him on his back and mounted him. He was nicely built and filled her comfortably. Bringing his hands up again to pleasure her bosom she smiled at him as she rode. It wasn’t too long again before she felt him swell and pulse inside her. She reached down and got herself off as he watched, wide-eyed.
As she laid on his chest she asked, “You said you hadn’t had much experience with sex. How much?”
He turned his head as he explained, “It was with the wife of another student at ministerial school. We only did a few times before she felt too guilty to continue. I never tried it with anyone else.”
Nan gave him a kiss, “Well I enjoyed this, for your information. I’d have you stay and we could do it again if I didn’t have to study for an exam tomorrow. I’m hoping we can maybe get started earlier next Sunday, that is if you want more.”
That brought a smile to his face and he nodded and gave her a kiss. She put on a robe and he put a towel around his waist and they went down to the shared bath and he had his first shower with another person. She noted that he was erect as she toweled him off and gave it a little more than a brief kiss. “That will be a treat for another time,” she thought with a smile.
Their Sunday afternoons became something she really looked forward to. He worked at developing her spirituality and she worked at developing his sexuality. Both of them were like sponges, absorbing these new and important things. One consequence, she became aware, was that the two of those things were coming together and their sex was becoming lovemaking, distinctly different than the fucking she did with other guys in between. They were becoming quite close.
Trent was pretty perceptive of feelings, something that had led him towards his chosen career. One afternoon, after an hour of conjugal bliss, he asked, “Something’s been bothering you more and more as we make love. Would you share it with me?”
“I’m not sure I can. It might change the way you look at me and feel about me and I can’t risk that. You’re just too damn important now.”
“I’m a little disappointed to hear that,” he said. “I thought we talked about how important it is to be nonjudgmental and accepting. You not have confidence in me?”
“It’s myself I don’t have confidence in,” she blurted.
He held her close and said, “Tell me. Whatever it is. I’ll still love you.”
She was wracked with a sob as she heard the L word, “I’m not the same woman during the week as I am here with you. I have sex a lot with other men almost every day. I’m kind of a slut, or maybe a whore because I get things from them in return. Not money but meals and gifts and other things I need. Okay, now I’ve admitted it and if you can’t put up with a woman who fucks around I’ll understand if you leave.” She buried her face in the pillow and sobbed some more.
Trent stroked her back gently and quietly for a bit, absorbing what he just heard. It wasn’t anything he’d expected so it was going to be a big bite to chew.
His ministerial training kicked in and he felt a bit of relief, because there was some action he could take. That always makes men feel better. He snuggled down next to her and spoke softly into her ear, “I do want to understand. Will you tell me how this came about? You know I’m a good listener.”
She began at the beginning and it was almost two hours later before she’d answered his gentle questions interspersed during her “confession”. He thought that it really was that, since she was revealing and releasing things that had been bottled up inside her for so long and trusting them to him.
Even though hearing some of the things she did got him erect, he did not make any moves toward coupling. If that’s what she wanted, he would provide it. He was reassuring and said loving things.