*Sneak Peek* 319 Winesap Lane

[CarlHoliday]

This is the first draft of Chapter 1 of a new long story I'm considering:

 

Jerry was just eighteen and in his first year at Warnton College. There was an innocence about him that I found sexually exciting. He was at my house for an interview to be a houseboy. I had recently bought the house at 319 Winesap Lane and, as it was much bigger than I needed, there was a need for help that far outweighed whatever privacy I might lose. Just by his appearance: long, sandy brown hair; steel blue eyes; small, perky nose; and thin lips, on top of a lithe frame of medium height, almost ensured I was going to have him taking up the bedroom on the second floor I had designated as the houseboy’s bedroom and study.

 

“Wow! This house is big,” he said. He was at the front door, on the covered porch. “Why style is it? Is it Victorian?”

 

“No, Queen Anne,” I said. His eyes were pulling me into their alluring depths. “Come inside. Did you have any trouble finding it?”

 

“No, there’s a lady in financial aid office who I guess lives around here. She told me how to get here. She said you need a houseboy. What will be my duties?”

 

“I need someone to help out around the house. It looks quite large from the outside, but it seems to get bigger inside. I’ve drawn up a list of duties that go with the position, so come on into my office and we’ll go through the interview first. If I think you’re the right boy for the job, I’ll let you look over the list and you can decide if you want the job. Come on, the office is in the back.”

 

We walked through the foyer, past the stairs to the upper floors and down the hall. On the left was the entryway to the living room and then on the right was the entry to the dining room with the long, polished cherry table that came with the house. At the end, instead of turning right into the kitchen and pantry, we went left down a short hall to the study, which I suppose originally was the master bedroom. A door on the right side went into a room I suppose was the nursery, but I had put a lot of exercise equipment into it. In the office I had a large oak desk over by the window and two overstuffed side chairs beside the fireplace. I sat down in one and offered the other to Jerry.

 

“The secretary over at financial aid said your name is Jerrold Alexander Peterson the Fourth; is that correct?”

 

“Yes, Professor Johnson.”

 

“I tell you what, why don’t we drop the Professor Johnson around the house.”

 

“Yes, sir.”

 

“What do you go by, Jerrold or Jerry?”

 

“I prefer Jerry.”

 

“Good, that works for me, too. Where are you from?”

 

“Appledale, Michigan. It’s a small town near Grand Rapids.”

 

“Why didn’t you go to a school in Michigan?”

 

“Well, all the men in the family have gone to Warnton. I guess you could say it’s a tradition that I felt I shouldn’t break.”

 

“Did you have the grades to get into Michigan or Michigan State?”

 

“Yes, sir, but my great-grandfather was rather insistent I come here. My dad wasn’t too particular where I went, but Gramps was downright adamant I come here. He even went so far as to offer to pay for part of my tuition, but, of course, he’s not in a financial position to do that now. He’s out of the apple business and living on a fixed income.”

 

“What scholarships do you have?”

 

“What with the variable nature of the fruit market my parents weren’t able to help out financially and I didn’t get any scholarships either, so that’s why I was looking for work-study, but Warnton doesn’t participate in the program. If I don’t find some sort of work, grants, or loans, I’ll have to go back home and maybe join the military or something like that.”

 

I suppose it helped that he was desperate for a job, so the next question would tell me just how desperate he was. I don’t know where this evilness was coming from, but Jerry’s body was sending signals my thirty-four-year-old mind was picking up on just like those same synapses responded to Stevie, Kiel, Tim, and Ricky when I was a teenager.

 

“So, Jerry, how’s your sex life?”

 

“My what?” Jerry asked, startled. His nervousness was fully apparent and I could see a bit of fear in his eyes. “What does that have to do with me getting this job?”

 

“Well, part of the job includes full room and board, so that means you will be able to bring someone over, if you’re so inclined. I just need to know if you’ll be bringing over a girl or a boy. I don’t mind which, I’m just concerned if you get overly involved on one of the living room sofas and whether the other person’s shirt is going to be on the floor. Now, if it’s a boy there won’t be anything wrong, but if it’s a girl, then I might have to ask you to go into your bedroom. Then there’s the problem with intercourse. Are you into fucking or do you primarily keep it to oral sex?”

 

The whole time he sat there in his chair staring at me and, now that I had finished, I wasn’t certain whether he was going to bolt or stay and answer my question. At this juncture, I really didn’t care, although he was still incredibly cute and was getting more attractive the longer he sat there across from me. I very much wanted to go over to him, kneel between his knees, and discover what was beginning to fill his jeans. I wanted that young man naked. Oh, what the heck, I’d let him keep his t-shirt, but that growing bulge in his jeans was begging for attention whether Jerry realized that or not.

 

“Can I ask you a question?” He asked. He nervously swallowed while continuing to stare at me.

 

“Sure, what?” I had a suspicion, but decided to let him play his card. Maybe, just maybe, he’d play an ace.

 

“Is it true you’re gay? My roommate in the dorm said the rumor on campus is that you’re gay? Of course, he didn’t use that word. You don’t have to tell me, but I was just wondering because of what you asked me. You don’t have to offer me the job, but, just for your information, I had a girlfriend back in Appledale. We didn’t do anything except kiss, though. I think she wanted more, but I wasn’t sure I wanted to get that involved since I was going to college out of state.”

 

“Well, Jerry, just for your information, I am gay.” No use in trying to fool the kid.

 

“If I take the job, will I have to sleep with you?”

 

“Why do you ask? I wouldn’t normally consider that part of the job.”

 

“Well, maybe, I’d like to find out what it’s like doing it with a guy and if you are gay, maybe, you’d want to do it with me if I lived here.”

 

So, there it was. He was a virgin, but uncertain whether he was gay or straight and willing to explore a bit with someone who might be inclined to show him the way to a man’s heart. The bulge in his jeans was certainly becoming more obvious. Whatever was going through his mind was sending signals directly to his cock, but we had lots of time and if he was interested in the job, we would have even more time to get to know each other. I hadn’t had a good fuck in over a year since the last time I went down to Florida to see Tim at the Naval Air Station.

 

“Well, before we get to that, how about you look over the job description? If you don’t think you’ll be able to handle the job, there’s no point in going further with this.”

 

Jerry took the paper and went down through the list of duties. I didn’t know what he was going to say. Since the house was big, and it was probably foolish for me to buy such a place to begin with, I felt a need to have help with the cleaning, general maintenance, kitchen and pantry duties, and conversation in the evenings. A roll in the hay was only an unexpected added benefit. If he has a nice cock, maybe he’d want to fuck. Whatever he might desire, I definitely had an interest in getting to know that cock of his.

 

“So, you’re basically looking for a servant.”

 

“Yes, that’s right. Do you have a problem with that?”

 

“Well, no, but you said I would have to maintain the pantry. What exactly do you mean by that?”

 

“Making certain we have the food items we need, both dry, refrigerated, and frozen.”

 

“Oh, okay, I can do that. What’s general maintenance?”

 

“Well, since this is a small town, there aren’t any gardeners. So you would have to tend to the lawn and flower beds. We’ll both keep up the shrubbery, but I’m not interested in planting flowers, weeding, and taking out the spent flowers. Though I am very interested in having the yard full of flowers. Then there’s the leaves in the fall. Also, you’ll be expected to monitor the condition of the house and let me know if we have to call in an electrician or a plumber. The furnace in the basement pretty much takes care of itself, but you would be required to go down there and sweep now and then.”

 

“Oh, okay, I guess I can do those things. I did a lot of that stuff at home, so I should be able to do it for you, too. This thing here about maintaining good study habits. What do you mean by that?”

 

“I want you to maintain your grades so you’ll be required to do all the studying you need to do to accomplish that.”

 

“Will I be required to maintain a certain GPA?”

 

“Jerry, the better you do here at Warnton, the better chance you have of getting the position you want after college, whether that is graduate school or a good job. Anything else?”

 

 “Sir, I’d like it if I could have it. I certainly could use the money you’re offering, especially the room and board. I’d probably be willing to do anything to get that, even have sex with you, if you’re thinking of doing that.”

 

“Jerry, I’m very much willing to hire you and as part of the deal I’ll give you an extra amount to cover whatever other school expenses you have so that you don’t have to get any loans. How does that sound?”

 

“Wow! That’s great. So, are we going to have sex, now?”

 

“No, not now. Do you have a car?” Hey, stupid, the kid wants to have sex with you. Go over and kneel in front of him, open his pants, and see what he has to offer. But, no, not right now. Later. Let Jerry get settled into the house. Give him the grand tour. Go slow. Don’t scare him off. Remember that rent boy from three years ago you rimmed before fucking? And, you told Tim you didn’t like to do that. Are you going to do that to Jerry before you fuck him? You are going to fuck him, right?

 

“Yes, I have a car.”

 

“Good, now go back to the dorm and get all your stuff. You can move in today. I’ll call the financial aid office and let them know I’ll be hiring you and that you’ll be moving in with me. I think this will work out just fine.”

 

He left and I sat there wondering why I hadn’t taken him upstairs to see his bedroom. That would have been a good time to get him naked, but there was plenty of time for that sort of thing. Frankly, I wasn’t in that much of a hurry. We’d get around to sex soon enough and he was going to find out if having gay sex was something he is was willing to get involved with. How was I going to go about this, though? He was a virgin. Other than having kissed a girl and probably not doing much more than a little petting, how was he going to be when I started undressing him?

 

Go slow. Remember how you were with Ricky? You drove him wild with anticipation, but when it finally happened life got in the way and you lost him forever. My mind was rolling all of this over as I tried to decide if I was going to turn this into to a daddy relationship or just leave it as I originally intended. I was a little young for a daddy role and certainly didn’t have the equipment for a decent job. Maybe just a blowjob today, just to release the tension.

 

**********

 

I couldn’t believe what financial aid was doing to Jerry. It was almost as if they wanted him to go back home. They weren’t going to offer him anything in the way of grants or loans. So, I went down to admin and went into the admissions office where I paid his tuition for the fall term and all the other fees that were required, which weren’t much since he wasn’t going to be living in the dorms. Now, all he would need is money for his books, note taking material, and whatever else he needed for the classes he had signed up for.

 

I made it back to the house just before he drove up. I asked if he had gotten everything and he said he did, which was a good thing because I had checked him out at residential life while I was down at the admin building settling his tuition situation. We carried all of his boxes up to the suite where he would be living and I went about helping him unpack. Many times I would be close to him at the pile of boxes when both of us happened to be there and there would be a scent of him in the air. I don’t know if it was the soap, after shave, shampoo, or his natural scent, but it was driving me crazy. I finally stopped and sat on the bed to watch finish.

 

“What’s wrong?” He asked while a strange look crossed his face.

 

“You, that’s what,” I said. I knew I should wait, go slow, give him a chance to react, but that smell around him permeated my very sense of being.

 

“What about me is wrong?”

 

“You have an odor I find very appealing. I don’t know what you do to cause it, but you’re driving me nuts in here.”

 

“You mean I stink?”

 

“No, Jerry, you definitely do not stink. If you came over here right now, I would probably push you down on the bed and try to discover what it is about you that I falling for.”

 

As I expected he stood over there by the door and the diminished stack of boxes staring at me. And, then he did something I didn’t expect. An expression of hesitation filled his face for a moment and then he came over to me. He pushed me back onto the bed and climbed on top of me. His mouth met my unready lips, but his kiss was soft and likeable. His lips lingered on mine while his tongue began to probe its way into my mouth. I could feel his erection as it began to grind into me. This was not a time to be pedantic. In my final moment of adult thought, I decided to let him have his way with me. If we were going to share cum, it would be his choice not mine.

 

After a few minutes he rolled off me and began to undress. He looked at me with desirous eyes and I followed suit. I pulled the bedcovers down and lay down on the sheet. Jerry came over and lay down on top of me. He paused for a moment.

 

“What do I do?” He asked. His eight or so inch uncut hard, thick cock was throbbing to the beat of his heart. It was going to feel so good buried in my ass. I was almost tempted to go over and kneel in front of him and take him right then.

 

“Whatever you want; you’re still a teenager with a raging hard-on that’s desiring relief.”

 

“I don’t know if I want to fuck right now.”

 

“Then we won’t. We can do that some other day when you’re ready to take that step. It’s a big step to give of yourself in that way. Why don’t you just lie on top of me and we can kiss for a while. While we’re doing that rub your cock against mine, you might discover you like doing that. The only rule in gay sex is you do what you want. We won’t ever do anything you don’t want to do. But, you have to talk to me and tell me what you want and don’t want. Okay?”

 

“Sure, thanks.”

 

And, so, we began to kiss, a lot and eventually he had his cum; two of them, in fact.

 

**********

 

We were in my study sitting in the side chairs. I thought about having a fire to celebrate Jerry’s first day with me, but it had been a rather warm day, so I settled for a good brandy in small snifters. Jerry seemed to appreciate the trust I was showing him by allowing him to drink alcohol in my home, but I told him that I was not a drunk and didn’t want him to be one either. Plus, I told him I was not opposed to him having weed in the house as long as he restricted his use to his rooms. He said he didn’t smoke that stuff and I chose to believe him. I told him anything else was totally forbidden and discovering it would result in immediate notification to the authorities and cessation of his employment and all privileges that went with that, which would mean his return to Michigan if the police didn’t have other ideas. He gave me his promise on that.

 

I was in red, blue, and gray tartan flannel pajamas while Jerry was wearing light blue boxers. I was sipping my brandy and watching Jerry. He was looking through a book he had picked up at the bookstore. It was for the Anthropology 101 course, one of the optional basic core subject classes required of all students. Classes for whatever major he might eventually choose wouldn’t be available to him until his junior year. Jerry had very little body hair, including only a sparse beard, which made his face a delight to kiss. The silkiness of his skin felt lovely as I caress him this morning when we had our first sexual encounter.

 

“What’s it like?” Jerry asked, unexpectedly breaking my concentration.

 

“What’s what like?” What indeed could he want to know that I had the ability to answer.

 

“Being fucked by a man. Does it hurt? I imagine it might, but your cock isn’t as long or thick as mine and I was wondering what it would feel like being in my butt. Do you go in and out like you would do with a girl? I’ve had big, hard shits; would it feel something like that?”

 

“Well, yes, it would be painful in the beginning. Like most things in life you need to learn how to do it. But, to take a cock into your ass Jerry, you have to understand that giving yourself to me, allowing me to have you in that very personal way, is something that you have to consider very carefully. There can only be one first time. If you allow me to be your first, I’ll be as tender as I can so that you enjoy it as much as possible for your first fuck, but it’s very important for you to think about wanting to do this. In many ways, being fucked is submitting yourself to the dominance of the other man. It’s not something to be taken lightly.”

 

He took a rather large swallow of brandy and sputtered from the burn of the alcohol in his throat. He looked at me with an expression I couldn’t place. As I had been speaking to him I could see his cock stirring in his boxers, but now it had settled back into some state of normalcy.

 

“You know, sir, you don’t have to sound so academic around me,” Jerry said with a wry smile.

 

“I’m a college professor; I make my money sounding academic, so get used to it.”

 

“Do you have a boyfriend?”

 

“Yes, his name is Tim; he’s in the Navy. I’ve known him since high school.”

 

“You don’t see him much, then.” Another swallow of brandy, a small one this time. He’s learning. Maybe tomorrow we’ll try a good single malt, that’ll get him to sputter, probably more like gag.

 

“No, maybe once or twice a year when I go down to Florida or he comes up here.”

 

“Do you have anyone local?”

 

“You.”

 

“No one else?”

 

“No, just you.”

 

“It must be lonely not having someone close to you. Do you go out to clubs?”

 

“There’s a couple in Rochester and maybe one or two Syracuse, but nothing close by. Being gay is mostly a lonely affair.”

 

“That sounds horrible. Do you want me to sleep with you?”

 

“You don’t have to. I’m pretty much used to being alone in my bed. Besides, I snore.”

 

“Can I have some more brandy? This is kind of nice. Mom made an apple brandy, but this is definitely different.”

 

“When’s your first class tomorrow?”

 

“Ten, it’s the anthropology one. A Professor Adams. Do you know anything about him?”

 

“Alice Adams is a nice woman and you’ll like her,” I said. I got up and went to the side table. The brandy bottle was half full, so we’d have to concentrate on getting it finished before it went bad. I poured some more into his glass and mine, put the bottle back on the table, and returned to my chair. “The only thing you need to know about Anthropology 101 is accumulation and regurgitation. Absorb all the lecture notes, assigned reading, do the two papers, and take the two tests. There’s very little thinking involved in any 101 class. What are your other classes tomorrow?”

 

“Just College Algebra 101 at one. The instructor is listed as staff. What’s that mean?”

 

“It’ll be a graduate student from Rochester or Syracuse. Math and science use a lot of them because the professors are usually concentrating on the more complicated subjects or research projects and can’t be bothered with basic classes. Accumulate and regurgitate will get you along just fine. Are you good at math?”

 

“Yeah, I don’t have any problem with math, but I didn’t take calculus in high school so they’re making me start all over here. Algebra is too easy; I might get bored. What’s cum taste like?”

 

It was startling how easily he switched back to talking about sex. Well, this was rather straight forward and had a simple answer. I said, “It has a complex flavor that is affected by what a person eats. Some say it’s an acquired taste, much like scotch whisky, but the only way you can find out is try it yourself. Why don’t you take a swallow of brandy and come over here?

 

“Yeah, now pull my pajama bottoms off. Go on, this is the easy part. Now, kneel between my knees and take my cock in your hand. That’s the object of your affection tonight. The most important part of this is to remember where your teeth are in relation to my cock. Teeth are not romantic. No biting anything down there. The most important nerve endings are around the head and your tongue needs to concentrate its efforts up there, but don’t neglect the shaft either. Focus on your lips pressing against that as you go up and down and try to get it as far back in your mouth as possible. In time you’ll be able to get it down your throat, which makes taking cum a lot easier. Go on get to work and remember you’re to focus on giving me pleasure that will be rewarded with a mouthful of cum. Don’t worry, I’ll let you know.”

 

“You know you do talk like a teacher.”

 

He started out slowly and I had to remind him a couple times to watch the teeth. From the shape of his mouth, he was able to take me quite deeply before gagging. I told him to be careful, but to keep trying to take me into his throat. Once he got a rhythm to his bobbing and was able to keep his teeth back on a consistent basis, I put my hands on his head and ran my fingers through his long hair. It felt satiny, which heightened my desire. Even though the brandy had dulled my senses a bit, the feelings he was creating was sharpening my awareness and it was beginning to be focused on the tip of my cock.

 

“Massage my balls,” I whispered.

 

He started doing that, which sent more signals from my brain down to my pleasure centers. I moved my hands around his head until I could hold it and help him in his efforts. His fingers were driving my nuts crazy and I was getting closer.

 

“Slow down just a bit. Oh, yes, just like that. Softly suck on the head like Tim does to me. Oh, Jerry, I’m going to cum. Take me. Take it all.”

 

And, he took me into his mouth, but didn’t swallow right off. I think he was sampling my taste. I took the offered opportunity and pulled him up to kiss him and taste myself on his tongue.

 

“Well, what do you think?” I asked after he broke the kiss. He stood, went back to his chair, and took a swallow of brandy.

 

“It’s definitely something different. The texture was surprising, but it wasn’t too bad. I can do that, again. Now, what about me?”

 

“Want to fuck?”

 

“What?”

 

“Do you want to fuck?”

 

“You mean you want me to fuck you?”

 

“Sure, you’ve got a great big cock that should feel good in my ass. Come on, let’s shut the house down for the night and we’ll go up to my bedroom. I’ll give you a few pointers on how to fuck a man and then you can get it done. And, if you want, you can sleep with me tonight. Okay?”

 

“Yes, sir, that sounds great. Sir? Can I call you by your name if we’re having sex? Sir seems so formal.”

 

“Geoff is fine.”

 

“Jerry and Geoffy. The two jays.”

 

“Never, ever call me Geoffy again. That will get you booted out of this house in an instant. And, it’s Geoff with a ‘G’, ‘G-E-O-F-F-R-E-Y’.”

 

“Oh, okay, Chaucer. I can remember that.”

 

“Chaucer? What’s a boy from Michigan doing with Chaucer?”

 

“Reading him. I read The Canterbury Tales when I was a junior and it wasn’t for a paper either, just for curiosity’s sake.”

 

“What’d you think about it?”

 

“It was different. I still have the book and read it now and then. I brought it with me because I thought I might need it in college.”

 

We finally made it up to my room where I took off my pajamas and lay down on the bed. When I rolled over to the nightstand Jerry gave me a quizzical look, but when I took out a condom and the lube I could tell he had no idea what was going to happen.

 

“Put a dab of lube on the head of your cock and spread it around, you’ll get better sensations when you’re fucking me,” I said as I handed the lube over to him. He did that and I handed the condom to him. “Go ahead and put it on.”

 

“You’re not going to get pregnant so why should I wear this?”

 

“Ever hear of AIDS?”

 

“That gay disease? Yeah, I’ve heard some things about it.”

 

“There is the belief that anal sex is a contributing factor to acquiring the disease. I’ve had a few cocks up my ass and remember when you have sex with someone, whether it is a man or a woman, you’re having sex with every person that other person has had sex with. Besides, do you want a shitty dick?”

 

“Oh, yeah, thanks, that’s a good idea. So, guys will have to use condoms from now on?”

 

“Well, if you’re going to let yourself be fucked, you’d better make sure the other person is going to use one. You can pick up a lot of things from a dick that’s been around town a couple times, just as you can get a lot of those same things from a cunt that’s been sleeping around, too. How’s that feel?”

 

“Tight.”

 

“Spread some lube on it, not too much because I won’t have any trouble handling your thickness. Give me the lube. Thanks.”

 

“What are you doing?”

 

“Lubing up just a little. A condom just isn’t the same as bare skin.”

 

“Then why are you making you wear one? I’m a virgin. I shouldn’t have to do it like this.”

 

“I’m just getting you in the habit. I want to keep you safe.”

 

“Oh, okay, but this seems a rather academic way of doing things. Don’t you ever stop being a professor?”

 

“Only when I having sex, now stick that big cock of yours in my hole.”

 

I lay back and pulled my knees up to my shoulders and he buried himself into me. He pulled out and sank back in all the while adjusting the way he was positioned over me. Soon he began to speed up and I could see it in the eyes, the desire to the possess me, to press his dominance deep into me and own my soul. I gave it freely as he increased his rhythm until I saw the strain of the coming orgasm spread across his face. His breathing deepened and he began to make unintelligible guttural sounds. I reached down and began to stroke my own cock, but knew he was going to blow first.

 

“Kiss me, Jerry, kiss me.”

 

He did and his pace quickened until his body froze as his cock throbbed deep inside me. He collapsed and I kissed him deeply. I let him lie there until he slipped out and I could extract myself from his embrace. I ran to the bathroom to take care of something that had become very urgent.

 

When I got back he was still lying on the bed. He had an impish expression and I smiled.

 

“Well, how was that?” I asked. I pulled the condom off and put it in the trash basket. I took the soapy wash cloth I had brought with me and washed his cock.

 

“Wow! That was more than I ever imagined it would be. When do we get to do that again?”

 

“Maybe next week. I like to fuck, but not that often. Even when I’m with Tim I don’t fuck all the time. Besides, you have to decide whether you’re going to let me fuck you.”

 

“Oh, yeah, there is that to consider, too. Would you mind if I didn’t want to be fucked?”

 

“No, like I said before, we only do the things you like to do. Okay?”

 

“Sure; what we did this morning was good and I kind of liked sucking your cock, so is it okay with you if that’s all we do besides when you let me fuck you?”

 

“Sure, and I can always suck your cock, too. I’m quite good at it so I’m sure you’ll enjoy it. Go rinse off your cock and let’s go to bed. Busy day tomorrow with the first day of school. I’ll be getting up at six-thirty because my first class is at eight.”

 

He went into the bathroom and then came back out after just a little bit. Unexpectedly, he left and I didn’t know what to do. I heard him going down the hall and down the stairs, so he must have been going back to his room, but since he left his boxers I had to assume he was going to return. Soon, he walked back into the room and I looked up at him.

 

“Had to get my toothbrush and floss,” he said. He went back into the bathroom.

 

When he came back to the bed he pulled back the bedcovers and got in. He snuggled up against me and lightly kissed me.

 

“Good night, sir, I had fun today and thank you for taking my cherry. I’m no longer a virgin and I feel wonderful. I just wish I could tell someone, but I suppose that’s not possible around here, is it?”

 

“’fraid not. There are a few gay and lesbian professors and I’m sure there are gay and lesbian students, but since no one goes out of their way to announce their orientation around Warnton, you just have to be careful who you tell. Good night, Jerry, pleasant dreams.”

 

“Oh, sir, you can be certain of that.”