"I'm sorry, Sylvia, but I still don't have the rent. The divorce my parents are going through is making things complicated. My Dad just moved out to his own apartment, and so they are short of money for a while."
My divorced landlady, Sylvia Stuart, is 44 years old, which I know because she told me once, saying that she tried to be honest in all things. She's pretty for her age, with a slender but shapely figure, and medium-length wavy dark hair just starting to go grey. That day, in fact, she was wearing a low-cut button-down blouse that revealed she wasn't wearing a bra to support her medium-sized and still mostly perky breasts. She was sitting at her work desk in her study as I stood right next to her, and so I had a good view. I could even see the tops of her areolas.
She looked up at me and caught me looking down her blouse. She looked both amused and angry at the same time. Her pretty face can change quickly from kind and flirty, to annoyed and angry, and as I told her I wasn't able to pay the $800 a month rent on the converted garage behind her upper middle-class suburban home this happened.
Sylvia said, without much sympathy, "Well, does that mean you're dropping out of the University? When am I going to get my money?"
"I hope I won't have to drop out," I said, rather desperately, hoping the fact that I was six-feet tall and handsome, and that she had flirted with me sometimes, might sway her. Although I was sometimes shy and awkward, I had noticed that my good-looking face and toned and somewhat tanned body sometimes influenced women in a positive way.
"But to save me from dropping out I'll really need your help as I try to get the money together. I've increased my hours I work at the restaurant, and I'm earning good tips, but...."
Sylvia sighed, and then finished my sentence for me, "You still don't have my money."
"No," I confessed, smiling and still trying to be charming, "I don't--yet. Do you have any jobs around your house that I could do for you. I'll do anything for you, Sylvia. Anything."
She looked dubious and still annoyed, but also somewhat charmed by my attempt to flirt with her. I'd said "anything" in a slightly suggestive way, but without I hoped going too far--and I could tell from her expression that she'd picked up on it.
"Well," she said, looking suddenly calculating, "There is one thing. As you know, I run my private art classes here, and we haven't had a male model in a few years. If you model for my students for 45 minutes I could take $50 off of the rent you owe me."
"Um," I said, remembering how I'd glimpsed one day, through the halfway opened curtains in her covered and glassed-in large patio in the back of her house, a nude and fairly attractive middle-aged woman. This was before I knew about Sylvia's art class, and I was amazed to see this blond woman of about 40 with generous breasts who that day was sitting on a platform with a blanket on it, with seven or eight adult students around her with their sketch pads and easels.
I didn't exactly peer in the window as I walked down the driveway, but I stopped for a minute and looked at her. Her pose was relaxed, with her legs spread exactly toward the window that I was at. Staring between her legs I saw the mound of her hairy blond pussy, with her pussy lips peeking through her slit. As I looked at her with desire, my cock hardening, I realized with a shock after several seconds that this woman was looking out the window at me. Thank goodness she wasn't offended, but instead seemed amused as she looked at me, and even smiled at me and gave me a wink, which made me smile back and blush, and then I immediately walked on.
Anyway, although I was somewhat confident knowing that I was reasonably handsome, I was shocked at the idea of being nude in front of Sylvia, as well as all of her students, one of whom was her own daughter Julie.
"You mean com--completely naked--um--nude?" I said, my confidence fading away as I stumbled over my words
"Of course," Sylvia said with a smile, clearly enjoying my shock at the idea of me stripping down naked in front of mostly strangers.
"I don't think I can do that," I said uncertainly.
Sylvia's face suddenly flashed with anger again, "Well then, you can start moving out today. And you can bet that I'm going to sue you and your parents in small claims court for all the back rent, plus any legal expenses."
"Wait," I said, desperate, and trying to smile again, "Wait. Maybe there's a compromise. How about if I just wear underwear?"
Sylvia laughed at me, rather cruelly, and then looked directly at my crotch in my jeans, which was just at her face level as she was sitting there. I actually had a slight bulge in my pants from the semi I'd gotten from looking at the tops of her breasts.
She then to my surprise reached out with both of her hands toward my crotch as if she might touch me there, but she didn't actually quite touch me, and said in a falsely sweet voice with her hands framing my crotch with her fingers shaped like a picture frame, "Nick, your penis is part of your anatomy. And my drawing classes teach people to draw the human anatomy--all of it."
I swallowed, and then said, "Well....Okay," and as she continued to frame my crotch like a work of art, I said, "But what if I--I mean, what if during the drawing class I get...."
Sylvia looked up at me and raised her eyebrows in mock surprise, and said, "Are you trying to say, 'what if my penis gets hard?'"
"I guess. Yeah," I said, "I mean, of course I wouldn't want it to, but as an 18-year old guy...."
Sylvia smiled, but again looked thoughtful and calculating, and said, "Well, I would warn them in advance that you've never modeled before. I could even warn them in advance that you getting erect is a possibility. If that happens we might just stop the session, but if all of them want to continue on we would give them that option. After all, a man's erection is an important thing to learn about too, both artistically and otherwise. Without men getting hard, after all, the human race can't really go on."
I laughed, but then sighed, and said, "But even if I do it, it's only fifty dollars. Fifty dollars out of the two months of rent I owe you..."
Suddenly my shoulders slumped. I felt defeated. Maybe I should just drop out and move back home.
But Sylvia picked up that I'd got from flirty to defeated, and suddenly switched herself to being more encouraging, saying, "Listen, Nick, I can take $100 off if you let my students take reference photos of you so that they can finish their work at home."
She may have meant that to be encouraging, but suddenly for me it had gone from bad to worse, and I said, "You mean you'll let your students take pictures of me completely naked?"
"Yes," she said, sounding like it was perfectly reasonable, "They'll keep their photos private, just for their own artistic practice. And I'll tell you what, I'll announce to my class that you're in danger of dropping out because of money, and pass a donation jar around for anyone to donate what they can to your cause. Some of my clients are pretty well off, and if you play your cards right you might even pick up most of a month's rent that way."
"Okay," I said, sort-of warming to the idea, but then I added, "Won't it be weird for your daughter to see me nude. I mean, even though she's a couple of years older than I am Julie seems kind of, I don't know...innocent?"
Sylvia's daughter Julie was a contrast to her mother in most ways. Although her Mom was quite pretty and outgoing, Julie was rather plain and shy. Julie was also about fifty pounds overweight. But I could tell from I first time met her that she quickly got a crush on me in her own awkward way, and that crush had grown in the three months I'd lived with them.
It was Sylvia's turn to sigh, as she said, "Yeah, you've got that right. She's never had a serious boyfriend. She's twenty years old, and I think it's well past time for her to see a man nude, even if it is in an art class. In fact, I think she'll really like it, because you can tell, can't you, that she really likes you?"
"Yeah, I noticed," I said, "But that makes it even more weird for me to show Julie my...dick."
Suddenly Sylvia seemed struck by an idea. You could almost see a lightbulb turning on over her head.
She said, "Hey, that's an idea. How about in addition to modeling you become Julie's first serious boyfriend?"
"What?" I said, and then quickly added, "I like Julie as a friend, but I just don't feel that way about her."
Sylvia again suddenly looked and sounded angry, and said, "Didn't you just tell me last week that your girlfriend broke up with you? Can't you take pity on my daughter and make her happy?"
This was not going in the direction I expected, and I said, "You mean pretend that I'm attracted to her?"
"Yes," Sylvia said, looking up at me again, and then making the stakes clear: "Depending on how well you do with that pretending, how far you take it, and how happy you can make her, that could make a difference in your debt to me. But she can never know that I've put you up to this."
"Okay," I heard myself saying, surprising even myself, "I'll ask her out on a date today."
Sylvia beamed in triumph, and said, "Good. I think we have an arrangement."
She got up from her chair, and once she was standing next to me she slowly and deliberately placed both of her hands on my crotch, studying me to see whether I was going to say or do anything about this uninvited touching. When I blushed, but didn't try to move away, my landlady smiled, and started more firmly feeling and rubbing my penis and my balls, slowly up and down through my pants.
I gasped, my cock getting hard under her fondling.
She looked pleased at my surprise, as she continued squeezing and holding my cock through my pants, studying my expression as she did so.
As my thick six and half-inch manhood with it's somewhat large cock head got hard under her touch, she whispered while looking into my eyes, "Good boy, Nick. As long as you do everything I ask, I don't think you'll have to drop out. Now as pleasant as your hard young cock feels to your landlady, I do have some work to do, which includes transferring money from my savings account into my checking account, since you can't pay your rent. And so now why don't you go ask Julie out on that date? And make it clear to her during the date that you're very interested in her sexually. Make it clear that you want to be her boyfriend."
*****
I stumbled out of Sylvia's study, at the same time humiliated and turned on, and went directly to Julie's door, which was closed. I'd been in theater in high school, and had taken a beginning acting class. Method acting involved channeling your real experiences and feelings into your role, and so I imagined how I felt about my girlfriend from high school who had gone to a different college, the one who had just broken up with me because she'd met another guy. My ex-girlfriend was really pretty, and I was desperate to get into her panties. If I used some of that feeling in creating my pretend feelings for Julie, hopefully without overdoing it, then it might work.
I knocked on Julie's door. She answered right away, and looked surprised and pleased to see me. She was wearing sweat pants and a loose blouse, both of which she filled out. I must have looked a little flushed and strange to her, because she looked at me oddly with her mousy face and long dark hair, and then I saw her glance down at my crotch--and I saw her look of surprise at seeing the outline of my full erection. Glancing down myself I saw that a slight outline of my circumcised cock head was visible through my pants, along with my rigid shaft.
"Hi Nick!" Julie said, blushing and looking back up into my eyes suddenly, "What's up?" and then she added with a nervous laugh, "Are you here to cry on my shoulder again about your ex-girlfriend breaking up with you?"
"No," I said, smiling, "I'm all done with that. I've actually been thinking that the best thing for me would be to go out on a date, and I was wondering if you'd be interested in going to a movie with me."
