The Deckhand Thursday Cruise Part 3
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The Deckhand - Thursday Cruise, Part 1 free porn video
After the Tuesday cruise, I headed home for dinner and a long soak in the tub. My body was a little sore, but my ass needed a thorough soaking if I was going to continue this three days a week. I have had my share of gang-bangs at college but usually took more time off in between them.
With these cruises, I was going to have to learn to pace myself better, or I may not be able to last through the rest of the summer. The problem was with no one other than myself; Grandpa was right when he said it, I am a cockslut. As I dozed off in the tub, I was wondering what the Thursday cruise group had in store for me.
I woke in lukewarm water and hit the drain as I stood to dry off my relaxed frame. I wrapped the towel around my waist and headed for bed, looking forward to a day at the hardware store.
The alarm went off at five-thirty, and I shut it off while pulling on a pair of shorts for the journey to the coffee pot. Mom had already been up, made coffee, and all I had to do was make my cup before heading for the shower. After the shower and a quick bowl of cereal, I was off to some mindless physical work.
The day went quickly, and I had a small mulch job to do for one of the customers. Mrs. Jennings was about the same age as my mother but still thought that she could seduce anyone in town. It was no surprise to me that she chose me for the job, as I was the only employee there that she hadn't shagged.
I showed up at Mrs. Jennings house and went to the front door and rang the bell. There was no answer, so I called the number they gave me, and after a few rings, she answered. I said, "Hi Mrs. Jennings, this is Steve from the hardware store. I've come to take care of your mulching."
"Oh hi Stevie, just come around back. The mulch and the work are back here, and I'm just relaxing by the pool," Mrs. Jennings replied.
I made my way around the yard to the gate of her eight-foot privacy fence and opened it to see her lying face-down by the pool in a thong. She raised off of the lounge chair to wave me over, which exposed her mediocre sized breasts. As I approached her, she did not attempt to cover herself and even stood to greet me. When I got within arms reach, Mrs. Jennings grabbed me in a hug while proclaiming, "It's so nice to see you, Stevie!"
I kept my arms at my side while offering, "It's nice to see you too, Mrs. Jennings."
She pulled back and countered, "We'll have no more of that Mrs. Jennings crap. My name is Doris, and I'll make sure you don't forget it."
I stood there for a moment, unsure what to say in response as she stared at me. Finally, I squeaked out, "Okay, Doris."
With that said, she turned and wiggled her fully exposed, plump derriere back toward her lounge chair. Once she settled back on her towel, Doris curled her finger at me. I slowly made my way to her and asked, "Do you just want another coat on the current mulch, or do you have a new area to do?"
I was about five feet from her chair when her finger began curling again, so I moved a little closer. I was now within arms reach, as I found out rather abruptly when she grabbed the front of my shorts. Her arm was just long enough to reach a belt-loop, and she used that to drag me over to her chair. Doris' hand moved down the front of my jeans, feeling for the outline of my cock. Once she found it, she grasped it tightly and whispered, "I want a coat over the current mulch first, then I'll take a little infiltration from this."
I stuttered, "I... I don't think... I shouldn't," before she cut me off.
Squeezing my cock firmly, she insisted, "The customer is always right, right? So unless you're gay, I expect that you'll enjoy servicing me the way I want. Especially with the tip you'll receive if you do it to my satisfaction."
Two words of her rant hit me square in the face. The first was 'gay,' and the second was 'tip.' If she found out that I was gay, then my parents and the rest of the town would know before I even finished this mulch job. Since I was already fornicating for money this summer, what difference did it make whether my customer was male or female as long as I used protection?
The other word got my attention because I could use all the tip money that I could get. So after my greed quickly overpowered my self-respect, I inquired, "Do you have protection?"
Doris smiled, and replied, "Of course I do, silly boy. Now go get that mulching done cause I need a good screw."
After she released my cock, I headed for the mulch and began the assignment. Doris made her way into the pool via the stairs, slowing progressing until her thong was underwater. Did I mention that that insignificant piece of material was white? I also found out that when dampened, it became transparent. Doris obviously knew this as she strutted toward me to ask, almost shyly, "Would you like a drink?"
She should have won the academy award for that acting. Here she was wearing only a see-through thong and pretending like she wasn't buck-fucking naked. As I just stared at her like she was crazy, she pulled her thong up until it vanished into her liberal labia. At this point, she may as well have removed them because everything was in view now. I suddenly spurt out, "Sure, I'll have a glass of ice water."
Doris turned and wagged her scrumptious ass, yes, I said scrumptious, all the way to the sliding glass door. I told myself that I could actually enjoy fucking her if I could do it from behind, and get myself into those perfect jiggling buttocks. She returned with a tray carrying a pitcher of ice water, a glass, and several assorted condoms.
I was three-quarters of the way through the project when she made her way to me. I paused as she handed me a full glass and noticed that her thong was gone, and she was leaking down the inside of her thighs. I chugged the water and then returned the glass to the tray before getting back to the task.
Doris shimmied that gelatin-like ass back to the table, and I found myself hardening at the thought of pounding it intensely. It took me about twenty more minutes to finish spreading the mulch and picking up the empty bags for disposal. When I finished, I headed back to Doris as she lay there on her belly with her legs spread, and asked, "May I use your shower to clean up a little?"
Doris just stood up and pulled my t-shirt over my head then dropped to her knees. She seductively unbuttoned my pants before sliding them and my underwear down to my ankles. She toyed with my semi-hardon for a moment before suggesting, "Kick off your shoes and socks, and jump into the pool with me to rinse off the sweat and dirt."
I did as Doris prompted and walked to the edge before diving into the deep end of the pool. As I made my way to the far edge, she dove in after me and came up right next to me. Her left hand grabbed the edge, and her right grabbed my slightly shrunken penis. The pool was a little chilly, but I was never attracted to women, to begin with, so that wasn't helping either. She moved in for a kiss, so I closed my eyes and imagined that it was Gary or Pat from yesterday on Grandpa's boat.
As our tongues collided, my prick began to rise to the occasion, somewhat. I started to caress Doris' ass with my free hand, hoping that that would move things along a little more quickly. She took the hint and asked, "I'm guessing that you're not a foreplay kind of guy."
I was back in High School for a moment, struggling to come up with an excuse for not being attracted to the girl I was dating. At that time, I wasn't sure why I didn't get turned on by her advances. Back in the present, I knew exactly why but couldn't say, so I had to improvise. That ass of hers did get me going, so I used that to get out of here.
I looked into Doris' eyes and begged, "My girl at school loves anal sex, so that is what we do most of the time, but her ass isn't half as desirable as yours. Would you be interested in letting me fuck that magnificent keister that you've been teasing me with all afternoon?"
Doris kissed me hard before uttering, "I 'll be right back with some lube," before she climbed out of the pool and ran into her house. I silently congratulated myself as I climbed up the ladder and headed for the table. I grabbed the condoms and a towel to spread out on the grass.
When Doris came back out of the house, she was slightly more controlled, but her nipples were clearly hard. She got down on her hand and knees on the towel, sucked my cock to hardness as I fingered her already lubed anus. I started with one finger but quickly added a second as she started to moan around my cock. Just as I was about to add a third, she began to cum and spat out my cock.
I kept pumping my fingers in her back door as she turned in anticipation of anal sex. I removed my fingers, pulled on a condom, and pressed the head into her anal ring. As the tip of my prick slipped inside her plump fanny, I let her adjust while placing light slaps across her shimmying rump. She began to moan again and lowered her face to the ground as she pushed back until my pole was fully entombed. With shaking legs, Doris pulled away before growling, "Fuck my ass, you little bastard!"
She clearly loved being fucked in the ass, so I grabbed her hips and took control of banging her. I started slowly, but her groans and cussing had me speeding up the pace quickly. I could tell she was on the edge of another climax, so I started alternately slapping her cheeks. She went over the edge again, but I didn't slow my pace. She started mumbling something incoherently, so I grabbed her hair and pulled her face off of the towel. Her words were clear now as she cussed, "You fucking bastard... fuck my ass hard and make me cum again!"
I kept ahold of her hair with one hand while smacking her fanny firmly with the other. I alternated hands every five or so smacks as she began to squirm. I was getting close too, so I released her hair and grabbed both shoulders as I went into jackhammer mode. Closing my eyes, I imagined that I was shagging Pat in his backyard Sunday night on our date. The image was so clear in my mind that I shot several streams of cum into the condom as Doris squirted her girl-cum all over the towel. She gradually collapsed flat onto the towel, and I went down with her from sheer exhaustion.
We lay there trying to catch our breath, before she managed, "You really do... know how to... fuck an ass, don't you?"
After a few more pants, I replied, "I try... I try."
My cock was soft enough that I could pull it and the condom out now without causing her discomfort. Once I sat up on my heels I poured my semen into the grass out of Doris' sight. That little move was one that a Professor at college taught me, to keep someone from using his spunk against him.
Then I walked over to my clothes and slipped the used condom into my shorts pocket as I dressed. When I looked back at Doris, she was on her side, flicking her clit while asking, "So when can I get another superb ass-fuck from you, Stevie?"
I smiled and answered, "Between my two jobs I don't have any free time, but if you hired me for more work through the hardware store, than I'm sure we could do it again."
Doris disappeared into the house as I finished dressing and returned with a check for the hardware store and a hundred dollar bill for me. She pushed them into my back pocket as she sucked my face one last time. Breaking away, she said, "No one has made me cum three times in a single session, in a very long time. So you can expect that I'll be contacting the hardware store for your services many more times this summer. Now scoot on home, before I have you bending me over the table."
I took my leave, half running toward the gate while thinking about nothing but money. I had become a male prostitute and seemed to be just fine with that label. Pulling into the driveway at home, I wondered what sort of sex maniacs I was sailing with tomorrow.
I woke Thursday morning at five and jumped into the shower for a hot soak and a quick all-over shave. When I finished, I slipped on my pink thong bathing suit and covered it up with my shorts and a t-shirt. I grabbed some coffee and a banana before heading to the marina to meet Grandpa.
Pulling into the parking lot, I noticed Grandpa had just parked, so I pulled in next to him. I hopped out of the car with my backpack and coffee and voiced, "Good morning, Grandpa! How are you this morning?"
"I'm doing well," he answered before grabbing me in a bear hug. He then asked, "So how is old Doris Jennings these days?"
"Really!" I replied before continuing, "Did you know as I was doing it? How the hell does information like that spread through this town so quickly? I assume you know that I used protection too?"
"You know how this town works, and with Doris walking around her back yard in nothing more than wide rubber-band all day, increased interest and viewers exponentially," Grandpa explained.
"Even with that privacy fence, she has to have balls of steel to walk around in that state of undress," I added.
Grandpa laughingly replied, "You should know since yours had to be slapping up against hers." After we both quit laughing, he continued, "The good thing is that this will do wonders for your reputation as a ladies man. At least the back-room whisperers will let go of the idea that you're gay now. I assume that was your reasoning for pounding her ass."
I answered quietly, "Yes, it was. She basically called me gay if I didn't want some, so I quickly devised the fucking-her-ass plan. She actually has quite a desirable ass, you know, and she is a masterful cocksucker."
"So how did you get her to go for anal sex?" Grandpa inquired.
"After staring at her ass the whole time I was spreading the mulch, I got a little chubby. So I created a lie about my girlfriend at school only letting me have her ass. Then I added that her ass was much hotter than my girl's, and that got her. It helped tremendously that she loves anal sex, and came three times during our session. She gave me a one hundred dollar tip, so I have a feeling that I will be getting quite a bit more work from her," I responded.
"I'm sure you will since her husband is out of town more than he's home, " Grandpa surmised.
As we boarded his boat, I asked Grandpa, "So, now that that is out of the way, what's the deal with this group of dirty old men?"
While we were removing the boat covers and airing out below deck, Grandpa gave me the skinny on the Thursday group. This group was only four as one of theirs recently passed unexpectedly. Grandpa had left it up to them to decide when another would be added and even gave them a list of prospects. It was quite surprising how many men wanted to join my grandfather's little groups. The Tuesday and Thursday groups were reserved, but Grandpa left Saturdays open to the first five that made it to the boat. Once we were all done with the prep and made some coffee, Grandpa sat me down to go over their particulars.
"Okay Stevie, this group is not as sexually charged as is Tuesday's. Their names in no particular order are Sam, Cesar, Joe, and Matt. They will all go either way and don't have any special needs or requirements. There is a lot more fishing going on on Thursdays than any other day, so don't expect the three and four-ways that you experienced on Tuesday, "Grandpa conveyed.
Shaking my head, I stated, "I understand, and that's fine with me given my summer slut schedule."
We both snickered about that for a minute before Grandpa continued, "But, they did seem excited last week when I told them about you."
"Either way, I'm in it for the tips and the tips, so bring them on," I reacted.
We both had another good laugh at my double entendre before we turned to see Joe heading up the dock. We headed over to greet him, and I helped him with his bag. Once Joe was on-board, Grandpa offered him some coffee while I stowed his belongings. While I was below, I heard Joe say to Grandpa that he needed to pee and would be right back.
As I was pretending to gather some of the fishing tackle, Joe came up behind me and began cupping both my butt-cheeks. I had hoped something like this would happen since I do work for tips. As he continued to paw at them, I unsnapped my shorts and pushed them to the floor.
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