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Watched a lady peg a guy. Then I got to fuck his ass.
Chapter 35:

I Get To Fuck Some Guy’s Ass

After having my way with four holes, one rubbed on my face, I was spent. I lay on the floor wondering what was next. This crazy enclave that I had ‘discovered’ was turning out to be a real ball-buster, in more ways than one! I struggled to my feet and collapsed on the couch.

Ginny got up and excused herself, saying “I’m gonna go get prepared for my surrogate time. You gonna be okay if I leave you alone with Mr. Sailor, Donna? Hopefully I’ll only be gone an hour or two.” “Sure thing, Mom. I’m good. How about you, Sailor?”

“Well, I’m okay. A little fuzzy at the moment but I’ll recover.” As my brain fog began to dissipate, I got curious about Ginny’s surrogate chore. “So, Ginny. You’re off to be a surrogate, huh? I’m intrigued about exactly how that works. Can you educate me?”

“Sure. What do you want to know? Ask away, Sailor.” “Okay. So, who are you going to see and what do you have to do, for starters?” Ginny explained “I’m covering for a girlfriend of mine. She was called away unexpectedly and her Partner for the week has made requests. She asked if I could cover for her until she gets back day after tomorrow. Since I don’t have a Partner this week, it’s like putting money in the bank. She’ll have to cover for me someday.”

“Ah, I see. This whole Partnering system is starting to fit together. So, who are you seeing and what requests do you have to fulfill?” “It’s a married guy, maybe 45 or 50 years old. He wants a blowjob to get him hardened up, then get pegged in the ass. He’s got the strap-on so I don’t even have to worry about that.”

“Riddle me this, Ginny: a blowjob and an ass fucking, right? Does that count as one or two requests?” “Ha! Sailor, you ask the most mundane questions! It depends on how much work is involved in getting him hard. If it’s just a quickie and he hardens right up, we consider that like an essential part of the task. Or sometimes it can become like a tip, for quality service. It all depends on the situation, but it’s always agreed on before the session ends.”

“Got it. But what happens to the absent partner’s requests for those two days she’s gone? Does she just forfeit those or is there some sort of credit balance in their account?” “Jesus, Donna! Where did you find this guy, huh? I thought you had filled him in on how partnering works. What gives?” Donna replied with a heavily defensive answer, while shooting a death wish look toward her mom. “For Christ’s sake, mom. I’ve only known him since noon. And much of that time has been spent actually doing things, not talking about them. Give me a break!”

Ginny turned her attention back to me. “Sailor, to answer your question, my girlfriend will have a credit balance in her ‘account’, as you call it. She can use that credit in any number of ways. It can be applied to the partner who created it, to any other partner in the future, or to any surrogacy requests he/she receives.”

Wow. This seemed like a pretty well thought out, well-oiled machine. I wondered how many government officials the local town officials had to pay in order to carry out this clearly illegal scheme. First there was the local constabulary, then the county officials, then district legislators, then statewide legislators. I wondered just how high up the political food chain this scheme went. Was the governor involved? And then, what about the Feds? The alphabet soup of the FBI, CIA, etc., etc. There had to be records kept. Raffle ticket sales income, credit accounts, who’s partnered with who … the list went on and on in my mind.

“One more question. What if there’s a disagreement about these ‘credit’ balances? If someone is denied their request, although they’ve paid for the raffle ticket, who determines the outcome?” Ginny looked bored at this point, almost circumspect that I was some sort of spy, sent to upend the good thing they had going. “You do ask the most invasive, detailed questions, Sailor. I’m beginning to wonder about you. But to answer your question, that’s actually part of my job. There’s a committee, appointed by the current town council members, who adjudicate those disagreements. It meets weekly and I’m the recording secretary. I’m the one who has to contact the parties with the committee’s decision.”

As she put her pierced earring in, she turned and walked into her bedroom. “I’m almost ready. You’ll have to do without the car for an hour or so. Will you and Sailor be okay, Donna?” I knew what would happen if Donna and I were left alone for an hour. I didn’t know what would happen if I went with Ginny, but I wanted to see surrogacy in action. I spoke up.

“Hey, Ginny, is there any rule about an outsider being involved in a surrogacy? I mean, I’d love to go with you, if that’s allowed.” “Holy shit, Donna! This guy’s living up to his reputation! Sailor, I’m okay with it, but it’s up to the person who made the request. If he says No, then you’ll have to wait in the car. You okay with that?”

“I’m good with it and would like to go with you, but I don’t want to abandon Donna.” Donna piped up “No, no, Sailor. By all means, go with mom. I’ll be fine here. I’m still coming down from the hard sex we’ve had plus I’ve got my vibrator just in case.” With that, Ginny grabbed her bag and we drove to be surrogates.

Ginny cleared it with Michael and we were ushered into his bungalow. We sat in his living room as Ginny and Michael went over the details. Agreed that Ginny was acting as a surrogate for Michaels Partner, whom he had “won” at the raffle. Agreed that his request was for a ‘suck till firm’ blowjob, then an ass fucking with a strap-on, which he provided.

With the details agreed upon, he asked if we’d like a drink, or just get down to business. Ginny glanced at me, I shrugged my shoulders and she said “Let’s get down to business, you horny old goat.” He suggested that we retire to the bedroom.

I sat in a small chair in the corner, eager to watch this unfold. Michael got his strap-on from the closet and put it on the bed as Ginny disrobed. Once Michael had his pants down, Ginny was on her knees with his limp cock in her mouth in record time. She cradled his balls in one hand as she started getting his cock firmed up. She worked it in and out, wrapping her lips tight around it, until it started to thicken up. She paused with her mouth and started stroking his dick with her hand, jacking him off. She’d alternate between that and thrusting her mouth onto his penis, massaging it with her tongue. Soon she got him to the ‘suck till firm’ stage.

She looked up at him and asked if he was good to go. He nodded his approval and helped her strap on the peg. Things were getting interesting. I had only seen pegs used in porn videos; never in real life.

He got on the bed on all fours and Ginny lubed up the peg. As she stepped between his legs, she pushed them open wider and dropped a generous dollop of lube on his anus. First she spread the lube around his hole, then pushed a finger in. She stroked it, soon getting two fingers in. She pulled his hips up to the right height and guided the peg into his asshole. It went in without too much resistance so she started moving it deeper with each stroke. Michael was loving this and started moaning, obviously in ecstasy.

It was interesting to see a hot forty-year-old woman butt fucking a fifty-five-year-old dad bod with a peg. He was really getting off on it and she was just going through the motions. Putting money in the bank, so to speak. She kept reaming his ass with the peg and soon started talking dirty to him.

“You like that, old man? You like feeling that rod sliding in and out of your asshole, don’t you? You gonna let me pound your ass hard, huh? You know I wanna slam my rod deep in your asshole and cum deep in there. I wanna fill your nasty ass with cum juice. I wanna dump my whole load deep up your ass.” Michael was moaning and rocking his hips in unison with Ginny’s peg. “Yes, yes!! Pound it all you want! I’ll be your ass slave all night. Take my ass, it’s all yours.”

I got stimulated as I watched this, my dick was bursting at the seams to escape. I unbuckled my belt and pulled him out. My little guy was about half way there and I started stroking him to firm him up. The jingling of my belt buckle caught the attention of Ginny and Michael. He fell forward onto his belly, exhausted. Ginny stepped back, eventually turning to sit on the bed next to Michael.

Shortly, Michael propped his head up on his crooked arm. “So, who’s your friend, Ginny?” “Oh, that’s Sailor. He’s new in town. Thought you said it would be okay if he stayed.” “Oh, Ginny. It’s fine that he’s here. I’m just wondering if he knows how to use that dick? You know, I just use the peg because I only bid on females at the auction. Appearances in the community, being married and all. But there’s a difference between a peg and a real live cock. If he’s willing, I’d love to have a live cock up my ass. What ’ya say, Mr. Sailor?”

Holding my nearly hard cock in my hand, it would be awkward to decline. “Get up on your hands and knees, old timer.” As he did so, I grabbed the lube and prepared my rod. I followed Ginny’s lead and made sure I got the lube in his anus with two fingers.

Then, I stepped up, spread his cheeks, and pushed the head of my dick into his hole. It went in easily and I began to fuck his ass. Gently at first, escalating into a full-on deep pounding, over and over, slamming deep into his ass. He loved it and responded by opening his ass wide open and moaning loudly. “Cum in my ass! Cum in my ass!! I want you to cum in there” he nearly shouted. “Dump your load up my ass!”

With his encouragement and the visual of me pounding his asshole, I couldn’t hold it any longer. I came in his ass with three squirts, each at the end of a balls deep thrust. As I pulled out and stepped back, he puckered his anus, letting my cum juice dribble down onto his balls. He reached around and pulled his cheeks apart to show me his gape, then tightened his hole up to expel more cum juice.

Michael slouched back down onto his belly. As Ginny removed the peg device, she broke the silence. “So, are you good, Michael? Request satisfied?” “Oh, yes. And then some. Many thanks.” “It didn’t take much to get you firmed up, so I’m just gonna count the blowjob as a freebie.” “Ah, good. Very nice of you.”

Michaell continued “You know, before you go, Mr. Sailor did an admirable job on my ass. I’ve already got a partner for the week but my wife … well, she gets sort of neglected sometimes. She doesn’t have a partner this week. I was just wondering about his availability to service my wife. I think she’d really like it. What do you think?”

Ginny and I glanced at each other. I had no clue what to say. Ginny, again, took the lead. “Well, Michael, Sailor isn’t really “official” if you will. He hasn’t ever bought a raffle ticket and he’s never officially put himself up for raffle either. So any sex between them would have to be just between them, outside of the raffle.” Michael responded “Well, if he’s willing, I’d like him to at least meet my wife to see if there’s anything there. What do you think, Sailor?”

“Well, Michael, I wouldn’t mind meeting with your wife but you have to know that I’ve been having sex all day. I don’t think there’s much life in my little guy. Certainly not enough to satisfy your wife tonight. And there are no guaranties. She may not like what she sees or vice versa.”

No sooner were the words out of my mouth, when Michael’s wife entered the bedroom. Ginny was getting her clothes on, Michael was laying on the bed buck naked, and I was searching for my clothes, still nude. “Hi Ginny. Hi Mr. Sailor. I’m Carol, Michael’s wife.”

Carol, like Michael, was in her late 50’s, brown hair sprinkled with some gray falling just below her ears. She had a reasonably attractive face but she was easily 50 to 75 pounds overweight. Her blouse and her pants were a size too small, accentuating her plump physique. Her boobs were large and hung down nearly to her rotund waist. Her thighs were beefy, signaling an awkward time finding enough room between them to actually find her sex box.

She examined me as I fumbled with my clothes. Her gaze started at my face, then drifted downward, stopping to examine my manhood. She stared at it for a bit too long, gave a wry grin and glanced over to Michael.

“I overheard your conversation. I think it’s sweet that Michael would think of me and recognize my needs and desires. Mr. Sailor, I’ve heard a lot about you around town and, after tonight’s performance, I’d be honored if we could find some time together. I’ve heard that you have an exquisite touch and always satisfy your partner. A romp in the hay with you would make me very happy.”

I was in an awkward position, having been “offered up” my Michael to service his wife. And here she was, extolling my virtues and requesting a roll in the hay. It’s not often that I pass on sex, but Carol didn’t seem to be very fuckable. Sure, she had three holes but two of them appeared to be nearly inaccessible. And her overall appearance certainly didn’t help. I had little or no interest in having sex with Carol but needed to find an acceptable way out.

“Nice to meet you, Carol. And thanks for the compliments, although remember, they’re just rumors. As you may have heard me say, I’m pretty well used up for the night. Maybe we can hook up another time?”

“I can’t wait” she exclaimed, with obvious joy and anticipation in her voice. “When can I look forward to your visit? How long are you in town for? Will you be at the raffle on Friday?”

“Whoa Nellie! That’s a lot of questions. You’re aware that I live on a boat, down at the marina? I have no real schedule and, being retired, I don’t make a lot of firm plans. I usually just live in the moment. So, if we’re going to hookup, it’ll have to happen by chance. I’m really not one to make dates. When I do, I usually forget or get tied up with something else. I tend to disappoint a lot of people.”

Her smiling, excited expression vanished from her face as it turned into a disappointed frown. I continued to pull my clothes on as she pondered her response. “Well, maybe I could meet you at the marina.” She wasn’t giving up easily, I could tell. She continued her plea “Or we could meet to have lunch or drinks. What would work best for you, Sailor?”

I was struggling to avoid any sort of definite plan, yet leave her dignity intact. “How about this, Carol? Let’s just let this ride for now and see what develops. I’m not certain how much longer I’m going to stay here and I wouldn’t want to make a date and then not show. That’s just rude. I’m hopeful that we’ll bump into each other around town – pun intended.”

Ginny had my back and broke in “You about ready to get back to your boat, Sailor? It’s dark out, getting late. And I have to get home to make sure Donna hasn’t invited all her friends over to party while mom’s away.” With that, we said our goodbyes and left.

On the short ride back to her place, Ginny was all talk. “So that’s how surrogacy works, Sailor. And thanks for stepping up to the plate by fucking the old guy’s ass. Saved me from having to go at it again with the peg. And it looks like we got you yet another set of holes to enjoy. What’d you think of Carol? She’s really nice. Kind, considerate, thoughtful. But Michael’s fetish with getting his ass pegged kinda ruined their sex life. Poor woman. She could use a good roll in the hay, especially with someone like you. You’d be doing her and Michael a huge favor. If you’re interested, I can help with the setup. Just say the word and consider it done.”

I was feeling at a loss for the “right” response. I really had little to no desire to spend an afternoon or evening working hard to satisfy some dowdy, overweight housewife’s sexual desires. I mean, why was this all up to me? Carol could easily buy a raffle ticket, use a vibrator or just casually hook up with a neighbor.

This town seemed to tolerate, even encourage, casual hookups. My brain was weighing all the pros and cons of the situation I was presented. On the plus side, sure, I’d get my rocks off. But I didn’t really need Carol to help with that. I would get to explore yet another set of holes, yet what if they didn’t meet my expectations? I would be helping to satisfy a horny, neglected housewife, but I’m not the only one in town who can do that.

It occurred to me that having sex with Carol would be totally outside of the clearly illegal raffle, but that nuance might be lost when this hedonistic house of cards finally fell. I was feeling a bit put upon being asked to perform like this. My mind flashed to the memory of my day with Carla, Abby and Crystal, the “welcoming committee”, as they openly discussed who I should hook up with right in front of me.

“Ginny, I really appreciate all that you’ve done so far. You’ve shared your daughter with me, you’ve cooked me a nice meal, you shared some incredible sex with me and you included me in your surrogacy run. I’m very grateful for all you’ve done. Thank you.

“As far as Carol goes, all I can say is that I’m not certain how much longer I’m going to be in town. I can’t describe it accurately, but I tend to simply vanish with no notice. Something just “clicks” in my psyche and I weigh anchor and disappear over the horizon. I have no real ties to any particular place and no real commitments to anyone. So I simply move on to the next port. I’d hate to make an appointment to meet with Carol, only to find myself five miles offshore when the time came.”

By then we had gotten to Ginny’s house. As we pulled up into the driveway she said “Well, it appears as if Donna has behaved herself. No wild party going on. Do you want to come in for a nightcap?” “Normally, I’d jump at the chance. But I’m kind of worn out for the day. I’d rather just get back to my boat if you don’t mind.” “No problem, Sailor. Let me just run in and check on Donna. Then I’ll drop you at the marina.”

Once we pulled into the marina parking lot, Ginny turned the motor off. She turned to me with that unmistakable look in her eyes. Then she leaned over and started kissing me, full on, warm, sloppy wet kisses. As she maneuvered her tongue inside my mouth, she simultaneously started unbuckling my belt.

Before I could really react, she had expertly freed my dick from its holster and bent over to suck it. She gave me a slow, sensuous blowjob, the teaser kind used as a “tip” after a rewarding partner session.
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