At the Captain’s Lounge I meet a lonely widow. I take her back to my boat where she gives me a blowjob and let's me pound her pussy until I'm done.
Chapter 80: I Fuck A Widow
By the time I arrived at the Captain’s Lounge party, it was already in full swing. It was Wednesday night and it must have been a full moon or something; the place was packed! There were easily 75 or 80 people there, double the usual. With so many people there, it was nearly impossible to identify any friendly faces. I squeezed through the crowd to the bar. The same cutie as Monday waited on me. “What’ll it be Captain?” “Same as Monday. A generous pour of single malt scotch, two ice cubes.” When she handed it to me, I asked how much. She smiled sweetly and shook her head side-to-side. “You’re paid ahead, Sailor. No charge.” I winked at her as I dropped a $20 into her tip jar.
“By the way, darling. What’s your name?” “I’m Alice.” I took her hand and leaned over to kiss the back of it. Very old fashioned, very formal, very memorable for a 20-year-old girl. She blushed with deep pink cheeks and looked at her feet, smiling. “Nice to actually meet you, Alice. I’m in a party mood, so you’ll probably see me often tonight.” “Single malt, two rocks. I got you covered, Sailor. It’ll be my pleasure to service you tonight.” Just as the words left her mouth, she realized what that sounded like. “Oh, no. I mean, what I meant to say….” I guffawed, gave her a wink, and turned away to lessen her embarrassment.
Other than Alice, I had only met Carrie, the twins and Ida. It was doubtful that Charlotte would be there. She was probably with the family tending to funeral stuff. A quick survey of the room didn’t reveal any of the people I had met. The room was very crowded, at capacity, and stuffy. I jostled my way through the crowd to the outside screened porch for some fresh air.
The screened porch ran along one side of the building, hanging over the water with boats in slips beyond. Very picturesque. It had a few tables and chairs and, even though there were a couple on “No Smoking” signs, it was used as the smoking porch. There were two round tables, each filled with 5 or 6 people, and two picnic tables, one empty and the last table had only one person sitting there.
“Hi. Mind if I join you?” The attractive 40-something year old woman motioned to a chair. “Not at all. Please join me. I’m Amanda. You must be new to the marina. I don’t think I’ve seen you around.” “Hi, Amanda. Yes, I’m Sailor and I pulled in, uh, what day is today?” “Wednesday.” “Ah, yes. Wednesday. Guess I pulled in on Sunday. Stopping here for a week or so. But the ambiance here and the top-notch Captain’s Lounge might make me rethink my departure date.” “Watch out, Sailor. This marina has a reputation of being a Velcro marina, if you know what I mean. Boaters tend to stay here longer than planned.”
Amanda and I sat and made small talk for a bit. Soon, my drink was empty, as was hers. “I’m about to brave the madding crowd inside and force my way over to the bar for a refill. May I brink you a refill, too?” “That would be perfect. I’m drinking a standard gin and tonic. Kinda boring, I know. But I like the taste and the gin gives me a good buzz.”
I squeezed through the crowd and found Alice at the bar. As soon as she spotted me approaching, she prepared my scotch. As she slid it across the bar, I also ordered the gin and tonic for Amanda. Alice’s eyebrows went up in surprise. In a teasing voice “So, you’re already cheating on me, huh? Is this for Amanda, out on the deck?” Damn. Alice was not only hot to look at, she was observant and had some brains. I teased her back. “I hear that it’s not cheating if your partner watches. So, keep your eye on me, OK? And what do I owe you for the drinks?” Again, she just shook her head no and dismissed me with a wave of her hand as she focused on the next customer.
Back on the outside screened deck with Amanda, we toasted each other with our virgin drinks. The deck was the unofficial smoking area and one man at the far end was puffing on a cigar. A couple others were either vaping or smoking cigarettes. “How would it go over if I lit a joint right now, Amanda?” She pondered for a moment before replying “You’d probably have a half dozen people crowd around asking for some. Weed is very prevalent here. Management, of course, frowns on it, but the boaters don’t give a fuck. Why? Do you have some?”
“I was a Boy Scout, Amanda. It’s a rare occasion when I’m not prepared. Of course I have some. Do you partake?” “I do sporadically. Not daily, heck, not even weekly when I think about it. I get high when all the conditions are comfortable and the risk is low. My advice to you would be to wait until either the crowd thins out or you’re on your way elsewhere. If you lit a joint right here, right now, it would be the talk of the marina for days. Ralph, the Dockmaster might even have some words with you about it.” “Got it. Thanks for the advice.”
Amanda was very pleasant looking. Not a flashy, model type. More of an above average next door neighbor type. She had a square face, narrow eyes, and full lips. Her hair was brown with some salty gray creeping in. It was cut to fall just to her shoulders and she had some wispy bangs. Overall, she was a solid 7 on a 10 scale. From what I could see as we were sitting there, she was dressed modestly, appropriate for a 40-something year old woman. Her blouse was buttoned up the front and the top two buttons were open, revealing some eye-catching cleavage formed by her generous chest.
We sat in silence, sipping our drinks as I racked my brain for some interesting small talk. I was coming up dry. Finally, she ventured forth with “Tell me, Sailor. You said you planned to stay a week or so. What’s your next destination?” “Ah … the next destination question. Honestly, my next destination is the next port I get to. Do you have any recommendations?”
“Actually, I’m trying to figure that out for myself. My husband and I arrived here last year, on our way to Mexico. Shortly after we got here, he fell ill. Seriously ill. His condition worsened and he rapidly went downhill to his death. He passed away 4 months ago and I’m still trying to put the pieces together.”
“Oh, my God! Amanda, that’s awful. I’m so sorry for your loss.” “Yes, thank you. It’s been tough but the boaters have all been very supportive. Unfortunately, my children are grown and live far our West. One in Colorado, the other in Washington state. I’m trying to decide whether to sell the boat and move out closer to my kids or move on and see what the future brings.”
“Gosh, Amanda. You’re in a tough spot, a real crossroads. Big decisions to make, loss of your husband, no family close by. I wish that there was something, anything, that I could do to help.”
Amanda shifted in her seat and took several long draws on her drink. The expression on her face changed subtly. She turned to me, lowered her voice and said “Well, there is something you can do.” Intrigued, I asked “What’s that? Name it. If I’m capable, I’ll help in any way I can.” “Would you mind if we got more drinks and went to your boat for that smoke? I’ve been drowning my troubles in alcohol and the pot might help my mind escape, even if just for one night. I hesitate to even ask. It seems like an imposition.”
Without responding, I stood up and grabbed our glasses. “I’ll get some drinks and meet you at the front door.” Alice saw me coming and had my drinks ready by the time I got through the crowd to the bar. With two scotches influencing my behavior, I turned on the flirt mode. “You’re on top tonight, Alice. I think I’m about to go cheat on you. Want to come watch so it’s not really cheating?” She flashed a smile from ear to ear. “Gosh, Sailor. This is so sudden. But I wouldn’t be able to just watch. I’d have to join in. And I’m still working. Sorry. Maybe another time.”
Once Amanda and I got settled into the cockpit, drinks in hand, I lit a joint. I took a few puffs and offered it to her. She tentatively took it and had several small draws, coughing between them. We continued to work on our drinks until we had finished the joint.
A feeling came over me and I twisted around and kissed her. I expected either a slap or an invitation. I got the latter. She reached her hand up around the back of my neck and pulled me in closer, kissing me savagely. Her tongue quickly found mine and we enjoyed a sloppy kiss. Breaking for a breath, we tilted our heads and did it again. As we kissed, my hands started roaming.
I slid my hand in the open top of her blouse and cupped her breast. Her nipples were hard and erect and her areolas were ribbed and hard. She was enjoying this and so was I. I fondled her breast and finally got to her nipple, squeezing it and rolling it between my fingers. All the while we locked in a passionate embrace.
By now, Amanda was making moaning sounds and our kissing was needing to get to the next level. She stopped rubbing her hands on my torso and found my belt buckle. Like a pro, she had him released without too much fuss. She bent over and started giving me a blowjob.
Her lips were wet and her mouth was sloppy from our make out session. Her mouth felt incredible on my cock as she started working her magic, stroking it in and out. The warm, wet feelings as she sucked me off were intense. She kept this up for a good 15 minutes. My dick was pulsing and throbbing in her mouth, wanting more.
Amanda took a break and reached for her drink. I did likewise saying “That was wonderful Amanda. You’re good at that and I appreciate it. May I return the favor?” As she stood up to drop her shorts, she replied “I’d love that. But I really want my pussy fucked, not a head job. Is that a problem?”
My shorts now on the floor, she lay on her back on the bench seat. I climbed between her legs, grabbed my dick and started rubbing it up and down her nicely shaved cunt. She was wetter then wet, all ready to go. I slipped the head of my dick into her pussy and she let out a gasp. “Did I hurt you?” “Oh, God no, Sailor. It’s just been so long. Keep going, keep going. I want you to pound me hard.”
So I did. I eased my rod into her inviting pussy, got a rhythm going, and ended up slamming my cock in hard and deep. It was taking all I had to thrust my hips against her pelvis, over and over. All the while she was gasping, moaning, Oh Yessing and sucking air in between her teeth. I knew I was doing a good job and she was enjoying it.
So was I. The thought of getting to pound this willing cunt, as much as I wanted, until I was done, resulted in a massive orgasm. Like a fire hose, I shot wad after wad of thick cum, filling up her pussy. I kept him inside her until he went limp. As I pulled him out, her gaping hole drained, streaming ropes of cum down to her asshole. She put her hand there and smeared my ejaculate all around her fuckbox. Then she licked her hand clean.