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Chapter 35, An Evening with Harry
An evening with Harry -- I stopped near Baltimore to sleep, it was not far to Philly, but I was tired and did not want to fall asleep at the wheel, and I could not move back into my college dorm until tomorrow so I would have to get a room somewhere, and Baltimore might be cheaper than Philly.
I found a cheap motel, the Stardust, and asked the woman at the desk where I should eat, and was there any night life in this town. She told me to go to the restaurant down the street, walking distance, where the full kitchen stayed open until 9 pm and after that the bar stayed open until 11:30 on weekdays, and 1:00 am on Friday and Saturday. Well, it was a weekday, and only 7:30 so I showered and walked down the street.
The restaurant was open, and, as promised, the food was good. Chicken and stuffing and mashed potatoes and salad. I by myself at a table for two, the waiter, who in the way of the moment, told me his name, Chip, was really cute, about 5' 6", blonde like me, kind of fem, good body, deep southern accent. He brought my check and I paid it, when he came back with my receipt, he said, "New around here, I have not seen you before."
"Just passing through," I said, "back on the road tomorrow. Staying at the Stardust Motel. The woman at the desk said this was the only game in town for a guy looking for some fun."
"Well," he said, "it is a lot more active on the weekends, but, just hang at the bar and things, will pick up in a few minutes, whatever you are into, you might find it, being young and good looking."
"If I were into guys, what are the odds?"
"If I was of interest to you, your odds are already 100%."
"I could be, what time do you get off?"
"I get off work when my last table is done, which, tonight, would appear to be you. The kitchen is closed, so no more need for a waiter, you can still get a burger and fries a half hour before closing at the bar, but that is it. And I get off the other way after I go home alone, or, after some guy helps me out."
"I would be happy to help you out," I said. "Your place or my motel room?"
"My place," he said. "I have lots of toys if you are into them."
"Ok, I have not played with a lot of toys, but I am willing to try."
So, we went further down the street to a house which appeared to have two apartments and went into the first floor apartment. The building was sort of run down, but the interior of the apartment was really nice, good furniture, art on the walls, oriental rug. The one bedroom had a queen sized bed, a nice bathroom, big closet and a bookcase with doors. We went into the bedroom, he opened the bookcase doors, and there was quite a collection of dildoes, cock rings, lubes, leather straps, vests, leather pants with a cut out for the ass, leather jocks, you name it.
"What is your pleasure?" he asked.
"No pain, just pleasure," I responded.
"Here is one of my favorites: the long double dildo. It is flexible in the middle so we can both have it up our asses, and lie face to face or back to back which because of how it will hit our prostates is really good. This shorter one is good for crotch to crotch, balls to balls, if we use the long one it tries to go too far, up the descending colon, which is not really very good for you, and runs the risk of a rupture and bleed -- guys do it and show you how long a dildo they can get in there, but it is not a good idea."
"Let's try the short one first, I have seen it done on the net, and it looks really hot to me." And we did. He put condoms on both ends of the dildo and we lay down on the floor on some towels. He stuck one end up my ass, it went in easy, and then slid down on his back toward me, inserting the dildo as he went. We scissored our legs and were balls to balls and by tilting our pelvises, ass to ass. Our cocks were both dripping pre-cum, his a lot more than mine, and we began moving slowly, trying to get in sync, which we eventually did. It really felt good, my cock was as hard as it ever gets without anyone touching it. His was pretty hard as well.
"Want to try another position?" he asked.
"No, I want to experience this one to the end. I want to see what it feels like when I cum with this thing up my ass."
"OK," he said, "let's move!" We did. Sometimes we were coordinated, sometimes not, but it was hot either way.
"I am going to cum," I said, "and I could cum just from the dildo, but a prostate cum, for me, is not as satisfying as when my cock is being stimulated, too, so I am going to jerk off."
"Go for it, and I will do the same." And we did. We cleaned up, traded contact info in case he came to Philly, and hugged each other goodbye. And then it was the final leg of my journey, the dorms opened to proctors the next morning and I was ready to be home.