By Mickey S

If you are under age, or live in an area where reading stories that include sex between males is illegal, or if you're not into this type of story, please leave. This is a fictional story and all characters and events are a figment of the author's imagination. My thanks to Tim and Drew for all of their help. The author retains all rights. No reproductions are allowed without the author's consent. Comments are appreciated at

Chapter 9

Over the next week I turned down two dates that Karen offered me. One was to be a naked waiter and party favor for a group of gay friends on the Upper West Side. In spite of my early sexual experiences with my old roommates, I wasn't a fan of group sex. Besides, in a business setting it was harder to control things with more than one client. Everyone has his own personal fantasies and no matter how well the scene is defined in advance it's only a matter of time before someone begins to ad lib. I'd barely been able to keep things on track in the father-son-schoolmate fantasy when the two clients wanted to bareback, but if there were four, five or more clients I'd be at their mercy.

And `at their mercy' was a good description of the other date Karen offered me. It was an S&M scene, and not just leather costuming. When she mentioned a sling in a dungeon I didn't have to hear anymore. I wasn't interested.

So when she called with a date for the afternoon of my dinner with Declan I wasn't in a very good position to say no.

"It's a brief scene although it is in the city. A big black dude wants to fuck a hot white boy in the Ramble."

"During the day? Does he want to get caught by the cops?"

"No, he doesn't. He says he knows it's dangerous in daylight but he gets off on the danger."

"Well, I'm not sure I do. I haven't been arrested yet and I mean to keep it that way."

"Don't worry, he's got more to lose than you do. The man is a pro football player."

"Really? What team?" Like I knew anything about football teams and players.

"You know I can't tell you that. But take my word for it, he's going to make sure you don't get caught."

So I agreed to the job. Teddy wasn't quite so amenable when I told him he'd have to stay home all day while I was at work and then again in the evening when I went out with Declan, but that was his job. When I reminded him the more time he spent baby-sitting the less he had to do chores it didn't make as much difference as I thought it might.

A little after one thirty Thursday afternoon I entered Central Park at W. 72 St. just across from the Dakota. The date was at two but I was early on purpose so I could have time to wander around Strawberry Fields, one of my favorite areas of the park. I stopped for a moment at the Imagine mosaic, the tribute to John Lennon, then moved deeper into the park to the rugged area north of the Lake known as the Ramble.

The Ramble was a legend among gay New Yorkers. It had been a cruising area since the early twentieth century, becoming notorious in the fifties and sixties. While not as popular as it had once been it was still a favorite for those in the city who liked anonymous outdoor sex. The general area had been pointed out to me once when I was with a friend and I'd been around the edges, but I'd never been in the dense underbrush where the cruising took place. The only directions I'd been given was to go to a spot about a hundred yards north of the castle that was on a high point on the shore of the Lake. All I knew about the client was that he was a big black guy around my age. I was wearing what he requested, baggy athletic shorts and a football jersey with the number 5 on it, so I was sure he'd find me. Besides, he'd seen my pictures on the web site.

I only saw one other guy as I walked through the woods and he was white, so I kept looking around. I'd heard the active time for cruising was at sunset or later, so I wasn't expecting much activity. After a few minutes I saw what had to be my client. Even at a distance he was a real giant. He came straight through the woods toward me and as he got close I guessed him to be around 6'6" and even in his track suit he appeared to be close to three hundred pounds of solid muscle. The man was huge.

He looked me up and down without a word and then motioned for me to turn around. I did a complete 360 and he nodded.


So much for conversation. He stepped up to me, put his hands on my shoulders and turned me around. He put his arms around my chest and pulled me back into him, grinding his pelvis into me. Because of the difference in our height his crotch was pushing into my lower back. I could feel his dick stiffening against me. With his right hand he reached under my shirt, grabbed the waistband of my shorts and yanked them down. They fell to my ankles. I wasn't wearing underwear, as requested, so the only cover I had left was my shirt and that didn't last long. With one swift motion he pulled the shirt over my head and tossed it to one side. He must have pulled his dick out of his pants because a second later I felt his hot, hard skin pressed against mine. He wrapped his right arm around me to pull me close and with the other manhandled my ass, squeezing the cheeks, He ran the head of his tool up and down the crack of my ass, pressing into it a little more each time.

It looked like there wouldn't be any more foreplay than conversation so I bent down, fumbled in my shorts and came up with a condom and a packet of lube which I held back over my shoulder. He brushed my hand away.

"Brought my own. I'd never fit my meat into one of them little things."

Usually I was able to get a look at the client's dick before we did anything but this time just going by feel I could tell his tool was in proportion to the rest of him. I'd experienced enough dicks of all sizes in all colors to not believe in stereotypes, but this black dick felt like one of the largest I'd ever dealt with. Knowing that I was going to get fucked this afternoon and anticipating that sex in the woods would provide very little foreplay, I'd stopped at my apartment when I got into the city and done a little stretching to loosen up. I was glad I did because after he put on his extra large condom he placed the head of his club to my pucker and pushed. I took deep breaths, willing my hole to open for him but he only slid in about an inch.

With his right arm still wrapped around me holding me in place, he put his left hand over my mouth and shoved his hips forward very hard. His dick ripped into me, impaling me in one thrust. I let out a muffled yell that would have been heard across the park on Fifth Avenue if it hadn't been for his hand. He didn't give me any time to get used to the feeling of his thick pole but pulled back until just the head was in me and then thrust back in , even harder this time if that was possible. In no time he was pistoning in and out of me, the force lifting me up onto my toes each time he pushed in. If he hadn't been holding me in place I'm sure he would have fucked me halfway across Central Park.

While the pain went away after a few minutes I never did get comfortable or experience any feeling of pleasure. At best it was uncomfortable. He kept up the hard, steady  pounding of my ass for nearly fifteen minutes, grunting and groaning all through it, with a few obscenities thrown in now and then, things like bitch, cunt, pussyboy, whore. That must have been his idea of pillow talk.

Finally with one last furious thrust which lifted me off my feet he froze, shooting his load into me. When he was done he pulled out and let go of me. I fell to the ground. He took off the condom and tossed it on the ground. As I got to my knees I got a look of what I'd been impaled on before he put it back in his pants. It wasn't as large as it had felt, probably only ten inches. Only. I'd never had one that large but as it had felt like a baseball bat when it was in me I was relieved to see that it was human-size.

"Thanks, that was just what I needed."

With that he tossed a few bills on the ground next to me and walked away. I pulled up my shorts and threw on my shirt, then picked up the money. Three hundred-dollar bills, a much larger tip than I was used to, but I felt I'd earned it.        

I stood on the subway ride down to Chelsea. Once in my apartment I stripped down, lay back on the bed, lifted and spread my legs and examined my hole with a hand mirror. It didn't look like any real damage had been done although the area around it was bruised. I took a few minutes to very gently rub in some skin cream with aloe then got dressed in my 'street clothes' and left.

As early rush hour traffic crawled north on Route 23 traffic I thought about what Livy had said about my career when she had visited. Maybe she was right and I should be using my time at the farm to figure out a new direction for my life. While I'd never loved being an escort it had at times been interesting and at times exciting. At its worst it was just a job. Occasionally having sex with someone who was not only unattractive but rather repulsive was a chore and unpleasant but it was bearable. But several of my recent dates bothered me a lot. The two guys who wanted to bareback, the flabby, married lawyer, the creepy doctor and today's rapist were just too much. A few scattered plain fucks with regular clients had been boring. The only pleasant dates had been the last two with PDB and while sweet, they weren't hot. It was time for me to find something else to do. I was getting too old for this shit.

I fixed Dad and Teddy a big salad and chicken stir-fry over rice for supper. I expected Teddy to spend mealtime complaining about having to do a double shift watching Dad but he was pretty quiet. He just wanted to know when I thought I'd be back and I told him I didn't know but it would probably be late. Surprisingly it was Dad who seemed unhappy with me being away all afternoon and again in the evening. I wasn't sure if it was because he missed me or he didn't like having to spend so much time with his surly grandson.

After a shower I was ready for my date with Declan. I had been thinking of it as a date even though I knew it wasn't. Besides, the word date had a very different connotation in my life but I couldn't think of anything else to call it.      
Since I had no idea where we were going Declan drove. He had chosen a new restaurant, or at least one that hadn't been there when I'd left home, for our dinner. As my butt hit the hard wooden chair I winced. Declan noticed.

"Are you in some kind of pain?"

"Not really. I slipped in the barn this afternoon and landed on my ass."

"Are you sure that's all it is? Want me to take a look at it?" he teased.

"That won't be necessary." I buried my nose in my menu hoping to cut off any further conversation about my sore ass. When the waitress came to take our orders it was clear Declan wasn't done with his teasing.

"Do you have any chairs with cushioned seats? My friend's hemorrhoids are acting up."

"Declan!" I felt like sliding under the table but he just laughed.

"I'm just kidding," he assured the waitress. "Actually he was butted by a bull and has a nasty bruise."

"The chairs in the bar are more comfortable. Why don't you switch them for yours?"

After ordering our food we did just that to Declan's amusement.

"I owe you for that."

"You sure do. If I hadn't spoken up you'd still be sitting on that hard wood chair."    

We had both ordered prime rib with baked potatoes with butter and sour cream.

"I'm going to have to lie to Dad about this, maybe tell him I had broiled Dover sole or something like that, or he'll be jealous." I grinned as the waitress served us. "Or maybe I won't lie and let him be jealous."

"You know, he can have beef now and then as long as it's lean."

"I know. I let him have beef and pork once a week each so he doesn't complain too much. The other nights I get creative with chicken and fish."

Declan spent the first half of our meal catching me up on various members of our high school class. They were mostly the jocks and cheerleaders, the popular kids that he had hung out with. I hadn't been even on the fringes of that crowd although I knew who they all were. I didn't really care what had happened to any of them but I enjoyed listening to Declan talk. They'd been his friends back then and though he was still in touch with many of them I didn't get the impression he was close to them now.

"But enough of the old crowd, Silas. The only two members of our class that matter to me tonight are sitting right here. I know all about one of them and next to nothing about the other. So, how about telling me a bit about what you've been doing all these years?"

"What do you want to know? I've already told you I've been living in New York and working in public relations."

"Well, that certainly fills in all the gaps. How about a few details, like where do you live, how do you live and what the fuck is public relations anyhow?"

So I told him about my apartment in Chelsea, my permanent student status and then went through my rehearsed vague bullshit about my so-called public relations job, giving clients ways to change their image through planning events to present them differently. I was hoping it would bore him and we could change the subject but he listened with rapt attention.

"I'm still not sure exactly what you do. For example, what was your meeting in the city about today?"

I'd mentioned in the car that I'd been in the city all afternoon. Now I had to make up a story about it.

"It was a new client, a pro football player. I met him in Central Park for lunch at Tavern on the Green." Again, close to the truth. The restaurant wasn't all that far from the Ramble.

"Really? Who was it? Maybe he's on my fantasy football team."

"I don't even know what that is but I can't divulge the names of my clients. Sorry."

"So that doesn't sound like work, lunch at a fancy restaurant with a pro athlete. Sounds like fun to me."

"You can have it. The guy was a real jerk. I'm not going to be working with him if I can help it."

"I'm not sensing much enthusiasm for your job. Don't you like what you do?"

"Well, I'm told I'm very good at it and it pays really well."

"That's not what I asked. I asked if you liked it."      

It wasn't a good day for me to be asked that question. My feelings toward the job were probably the most negative I could ever recall.

"To be honest, no, there isn't much I like about it, especially lately. It used to be that now and then I'd feel like I was making a difference in someone's life, giving them a chance to be seen the way they wanted, even if just for a moment. But lately my clients seem to be self-indulgent asses, with a few exceptions of course."

PDB was one of those exceptions. While I didn't approve of his cheating on his wife with me, at least he had used his dates with me as a means to experience something that he'd missed in his life so he could settle down and get back to enjoying what he had. He was the kind of client that made me feel good about my career, but they were very few and far between in recent times.  

"So maybe you should try something else if you're that unhappy with what you do. Life is too short to spend so much time doing something that isn't meaningful for you. You should try to find something that lets you be who you are. Do you have any training for anything else?"

"That's the problem, I have training for everything. You name it and I've taken a course in it, but my interest doesn't last long in any one field. Enough of my boring life, though. Your turn, time for you to open up."

"Well, you already know a lot about me and my career."

"How did you decide you wanted to be a nurse? When did you know?"

"I feel like I've always known. My aunt is a nurse and I've always respected her a lot. I just love taking care of people."

"So why not become a doctor?"

"Everyone asks that, especially my parents. Like it's okay for a woman to be a nurse but a man has to aim higher. But I enjoy hands-on care, not directing that care from a distance the way doctors do. In the beginning I worked as a staff nurse in the hospital for a few years but I like home care even better. In the hospital the patient is just a sick person in a bed. At their home you're treating a whole person, not just a disease. You can see how what you're doing helps them live their life."

"You're a good person, Declan. So how come you're not married? My dad says you were engaged a while back, or is that too sensitive a subject?"

"It was for a while but I'm okay with it now. For a long time, both in school and later, I was quite the player. Sex was fun, dating was fun and I did lots of both. But I really thought Kara was the one. Apparently she didn't feel the same way about me."

"I'm sorry."

"It's just as well." He shrugged. "It turned out she wasn't the person I thought she was so it's a good thing I found out in time."

"So you're playing the field again?"

"Not as much as before, my recent Hooters experience aside. I've sown my wild oats and now I'd really like to settle down. And what about you? How come a bright, good-looking guy like you is still unmarried at 32?"

"Well, first off, although they've come close to doing it, New York and New Jersey would still have to change their laws in order for me to get married. You see, I'm gay." I'd decided when we first made this date that this would be a good time to come out to him, away from the house.

He raised his eyebrows but didn't seem shocked.

"I was wondering about that. Back in high school I thought you might be."

"Really? What would have made you think that?" I was more surprised that he had noticed me enough to form an opinion like that than anything else.

"Oh, nothing obvious but I knew a couple of girls who liked you and they were frustrated because they couldn't get anywhere with you. So it made me wonder why."

"Which girls?" I was amazed to hear that there had been girls interested in me. But then I had been living in a pretty closed off kind of world with walls up to keep others out.

"It doesn't matter, especially now that they're both married and you're gay. So, you can't get married because of the law. Does that mean you would be if you could?"

"No, that's the other snag. Even if the laws changed I'd need to be in a relationship in order to get married."

"So let me rephrase my original question. How come a bright, good-looking guy like you living in the heart of gay New York is still unattached at 32?"

"Now you're starting to sound like my friend Livy. Say, how would you like to come to the farm Saturday afternoon? We're having a little family cook-out and you can meet Livy." I'd been hoping for an opening to invite him.

"I'd love to but I have to put in an appearance at my parents' first. They're having their usual huge family get-together."

I couldn't very well argue against that since I'd made a point of telling Teddy that family was important on holidays.

"You have a big family?"

"Two older brothers, an older sister and a younger sister, all married. Between them I have eight nieces and nephews. Throw in a few aunts, uncles and cousins and you've got quite a crowd. Once I've shown up and said hello to everyone I can slip out without being missed."

After dinner we went to the Blarney Stone and continued our conversation. We'd split a bottle of merlot at dinner so I had a couple more glasses of that. Since Declan was driving he'd only had two glasses of wine with dinner and had one more at the bar, sipping it as we talked. This time we talked less about our lives and more about our interests in things like books, music and movies. We even got into politics a little, although that was always a touchy subject unless you knew the other person's inclinations at the start. By the time we left around eleven o'clock we were past being old acquaintances and on our way to being friends.
Declan dropped me off, promising to be back in twelve hours for his appointment with Dad. As I walked to the house I noticed a light was on in Teddy's room. I was glad he was upstairs where I wouldn't have to talk to him. I was on a high from a wonderful night out and didn't want his usual surly mood to put a damper on it. I poured myself an ample brandy and went out onto the front porch where I sat in the dark, enjoying the night air and reflecting on the evening.

I was thinking that if I didn't live in New York Declan and I could become great friends. Of course, if he were gay we could become a lot more than friends as far as I was concerned. But I did live in New York and he wasn't gay, so that wasn't going to happen. It was a nice dream, though. And for at least as long as I was staying on the farm it would be nice to have a friend nearby.

I was just about to go to bed when a car came down the road and turned into the driveway. At first I thought it was just someone who was lost and turning around, but the rear door on the far side opened, someone got out and then slammed the door a bit harder than was necessary. In the few seconds the door was open the light showed several people in the car. The car backed out and headed toward town while a dark figure came across the lawn toward me. As he started up the steps to the porch I saw it was Teddy.

"Where the hell have you been?" I asked as I got up.

His foot missed a step and he went down, banging a knee on the step.

"Jesus! Are you trying to give me a heart attack hiding in the dark like that?"

"I thought you were upstairs in your room, which is where you're supposed to be. What are you doing out?"

"Don't have a cow, man. Gramps doesn't need a baby-sitter, especially when he's sleeping. He'll be the first to tell you that. I waited until he went to bed and then called my friends to come get me."

"I know Dad's said several times he doesn't have to be watched but you'll notice he hasn't sent you home, so deep down he realizes he does need you here."

"Bullshit, you're both acting like old ladies." He pushed past me and went into the house. I followed him as he stumbled up the stairs.

"Have you been drinking?"

"Leave me alone, asshole. You're not my mother."

"No but I am responsible for you while you're here."

"Responsible?" He opened his door, stopped and turned in the doorway and faced me. "I'm the one keeping an eye on Gramps while you're out whoring around."

"What are you talking about? I go to work a few times a week. Tonight was the first time since you've been here that I went out with a friend."

He went across the room, pulled some papers from his top dresser drawer and came back, shoving them at me.

"You call this work, Uncle Silas? Or maybe I should call you Dream Date #5?"

I looked at the papers and saw they were printouts of the pictures Livy had taken plus my page on the Dream Date web site.

"How did you get these?"

"You never heard of putting a password on your computer? Anybody can just turn it on and see whatever you've been looking at."

"You've been going through my room and my computer?"

"Hey, I'm living in a strange house with a faggot I barely know. I like to know who I'm dealing with."

"You had no right to invade my privacy."

"And you've got no right to treat me like a slave around here but you do."

"A slave? I've treated you like family, only you're getting paid for everything you do."

"Yeah, like being part of a prostitute's family is what I want. Tell you what, stay off my back the rest of the summer and the old man doesn't have to know his son's a whore."

"You're not going to tell him that, Teddy. He's your grandfather and he's got a bum heart. You must care something for his well-being."

"I do, but now we'll see just how much you care about him."

He shut the door in my face, leaving me standing there steaming.