Tales of Dirty Old Man Ch. 08

I describe myself as a wannabe Dirty old man, not because I am one, but because as my best friend Karen keeps telling me, there is no higher accolade and so I should aim to be one.

This is the eighth chapter in this series - I recommend you to read the previous chapters in order before this one.

I can't thank Romantic1 enough for the time he spent reviewing and editing this and the previous chapters

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When I managed to get my breath back I said, "Holy fuck that was fun."

She said, "Fun! That was fucking brilliant."

After a pause while we kissed, she looked at me seriously, "I think that was the one. I know it's too soon but suddenly I really feel pregnant and I didn't before you dumped your cum inside me."

"God, I really hope so for both of you - for all of us."

We lay connected until I slowly lost my erection then we curled up in each other's arms and dozed until Simone returned.

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Family Rules

Simone gave us both a kiss. "Wake up sleepy heads, Pete is looking for his wife and I want my dirty old man."

Angie told us, "I need a shower first," and hopped out of bed. She scurried off to the bathroom. Presently we heard her singing happily in the shower.

Simone curled up beside me and I stroked her hair. She smiled contentedly and asked, "Did you have fun making a baby?"

"We did, but I will be glad when it's over and I can spend all my time with you."

"You won't forget our promise to Lisette?"

"I haven't, even so it will be nice to take it easy for a few days. I'm beginning to feel every one of my fifty years."

"Is it possible that Angie could be pregnant yet?"

"Yes, she thinks it's possible. I do hope so. If not, and it doesn't happen in the next couple of days, we will need to think about a repeat performance next month."

"Oh that's ok."

"If that's the case then let's have some fun. We could visit them in Dubai and have a holiday at the same time?"

I thought about it for a bit longer and continued, "I'm going to plan for a week away whatever the outcome is."

Angie called out that the shower was free, and Simone thanked her. I got up and headed to the shower. Simone followed and sat on the floor and we continued our conversation.

I left the shower door open enough to hear her. "I have a couple of friends I would like to invite to the wedding if you don't mind?"

I called back, "Why would I mind. You just need to give the names to Kirsten."

She replied, "I will. I'm looking forward to meeting her in person."

"You will love her, everyone does."

"So she takes after you, because everybody loves you!"

There was something in the way she said that last part, which made me pause. I looked down at her sitting on the floor. She had her knees tucked up and her arms wrapped round them. She was looking a bit nervous and worried. I quickly rinsed off and stepped out of the shower. Simone stood and with a smile handed me a towel. I wrapped it round myself and led her back to the bed.

As I dried, she sat on the end of the bed absentmindedly sucking on a lock of hair. I knelt at her feet and took her hands in mine.

I asked her, "Are you alright? I get the feeling you are worried about something?"

She looked at me with tears in her eyes. "I love you so much it hurts. But everyone you meet wants to love you. I'm scared that I won't be able to cope with that!"

I wiped a tear away, "You will never have to worry about that. You will always be the one for me. Ros knew she was the one when she was alive. I never ever did anything that we hadn't discussed or she disapproved of."

I eased myself into a more comfortable position, and Simone joined me.

"All you have to do is say no, and that's the end of anything you're concerned about."

"I just say 'no'?"

"That's right!"

"Ok then, no to Lisette!"

"Agreed, we will tell her as soon as we get back to town. I would like to offer to send her on a nice holiday. We did promise her one."

Simone looked at me with love in her eyes. "And that's why Lisette will be a 'yes.' You always want to help people and you want nothing in return. No wonder they all fall in love with you."

I just shrugged; there wasn't much I could say.

"What would have happened if I had said no to Angie's baby?"

"Then that would have been the end of it. I need your permission to make love to another woman, regardless of how long I've known them. Although I would have been sad that I couldn't help them."

I continued, "You do realize that this works both ways?"

She nodded, "Of course I do, and I wouldn't have it any other way. I do have one big question, we sleep with members of the family, how does that work? "

"Basically, in the same way. Julia came up with the best answer to that question years ago. Each time someone joins the family we all give our approval and reset our boundaries."

"I think I get it, so if I were to say you can sleep with Julia but only if I am with you that would be a boundary?"

"That's the idea. If you think about it, we have been setting unofficial boundaries all week. Look, the boundaries we set are very important to all of us in the family."

I sat for a moment gathering my thoughts. In a way this was new to me as well. Previously Ros had set most of our boundaries with our relationships inside and outside of the family. I needed to think how to put into words the actions I had been doing for a long time, and I needed some help.

"I'm not explaining this very well. I think we need to talk to Angie."

I quickly pulled on some clean clothes and we went to find Angie. We found her with Peter in the wheelhouse.

"Angie I need your help. We are having THE conversation."

Angie looked at me with sympathy in her eyes. "Oh God, and you haven't got Ros to help you. She was so good at explaining everything to new family members."

She continued and then gestured for Simone to follow her, "For this we will need a bottle of wine. Let's get comfortable in the main cabin, and I will do my best."

The girls went down to the cabin. I paused for a moment with Pete. On the chart I indicated a nice mooring in the small town of St Raphael, a few hours away.

"That's our destination, call me when we get close. We should get there mid afternoon"

I joined the girls on the sofa. I was handed a glass of wine.

I said, "Angie, I think I know most of it but I'm not sure how to explain it."

She laughed at my statement and said to Simone, "That's Andy for you, a typical man. He created almost all of the family guidelines, but hasn't a clue how to explain them."

She continued to me, "You do realize, all Ros ever did was formalize your attitude to life."

She sipped from her glass and continued. "When I first met Ros and Andy, Pete and I were in a bad place. They solved our issues and invited me to join the family. Ros sat me down and explained the family. She summed it up in two words Honesty and Respect."

She held up a finger, "Firstly, we are totally honest to all other family members in regards to our relationships. No one has ever had a secret affair. But we have all had lots of lovers from inside and outside the family."

She held up a second finger, "But, and this is the respect part, never without our partner's permission. Before I asked Andy if I could have a baby with him, Pete and I asked your permission. If you had said no, we wouldn't have asked him."

She paused for another sip.

"Each time I was introduced to a family member, we would define our relationship boundaries. Some we sleep with, some we don't, but we are all friends. Andy and Ros were the only couple who we all slept with."

Simone asked me, "Does that mean I need to sleep with them all?"

I responded with emotion in my voice, "Good god no! Joining the family is not an open invitation for sex. We're not a glorified swingers club. Each time we meet a new family member, it's up you to decide to what level you want to take the relationship. You set your own boundaries and everyone will respect them. Think about Julia and Mike, both of them asked your permission to sleep with us. I already had Mike's permission to sleep with Julia. But none of us just assumed you would be happy with that."

"I'm glad I did, I really love them."

"And that's the point, it was your choice. Remember you asked Mike not to cum inside you?"

"Yes."

"That was you setting a relationship boundary with him, and only you can change it."

Angie interrupted, "I have one with all my lovers. My ass is off limits; I only do anal with Pete."

"I don't remember that one," I said.

"Oh, you are the other exception, only you never seemed to want to, so the boundary never came up as an issue between us."

Angie held up a third finger. "There is one other very important rule. We don't have unprotected sex with anyone outside the family. And we all have regular checkups."

Simone looked at me with a worried expression. "But we had unprotected sex."

"I know. I broke the rules, but I wasn't thinking about the family then. Don't worry the hospital will have checked you for STD's after your assault. You told me that I was your first since then, so we know it not to be an issue. But we will schedule an appointment for both of us. I haven't been checked since Ros died. I'm not worried, the only person I slept with in the four years was an old friend, and we used protection."

"Is that why you wore a condom with Lisette?"

"In part, plus she wasn't sure about her birth control. I think Julia suggested that she get herself checked and her birth control sorted out."

Angie said, "She did, I was there when she spoke to her. Lisette said she would do it immediately."

"That's good to know."

Simone kissed Angie and then me. "Thank you both; I feel a lot happier now." She looked at me, "Can I try setting some boundaries for you?"

"Of course."

"You have my permission to sleep with Angie and Julia whenever you want."

Angie said, "Thank you," and hugged her.

"And you have mine to sleep with Pete and Mike." I told her.

Then I asked her, "What do you want to do about Lisette?"

She thought about it for a moment, and then replied. "For the moment you can sleep with her. But I want to be with you or nearby, and I'd like to be asked first."

"I agree and the same rules apply to you and her."

"Oh, do we need to set boundaries for lovers of the same sex?"

Angie replied, "Some of us do, some don't. Pete and I don't. But in Lisette's case, as she not yet a family member it's probably wise."

I said, "Ros never needed to set same sex boundaries for me. I've never been interested in men as a sexual partner."

Simone asked, "How do you remember all the different boundary options that must exist."

I laughed, "With difficulty sometimes. Ros seemed to be able to remember them all."

Angie said, "Kirsten found a list in one of Ros's note books. There's a copy on the web page we can all update. The list helps manage expectations between all the family members, particularly when we know we're apt to be with someone we haven't seen for a while and need a refresher on their limits."

"Christ, am I out of date!"

I drank the last of my glass and the bottle was empty. I asked if we wanted another one, and I got a yes.

I returned with the fresh bottle. As I filled the glasses, Simone was asking Angie an interesting question that had a lot of potential for me.

"So do you enjoy anal sex?"

"Oh, God yes, the orgasms are so intense."

"The men who forced me to try it were too rough and didn't care if it hurt me."

"I'm sorry; you really need to try it again with a lover you trust. That's why I only do it with Pete; he's careful and understands my anatomy."

Angie looked at me shyly, "But I would let you any time if you wanted to. I know you would be so good." I smiled at the compliment and the trust it implied.

Simone looked at me, "Do you think we could try it sometime soon?"

I felt a throb of anticipation surge through my cock. "Of course we can. You just need to tell me when you really want to try it. There is no pressure on my part."

She smiled as she placed a hand in my lap and felt my cock stirring. "I think he is happy at the thought of fucking my ass."

"He's always happy at the thought of fucking any part of you."

Simone bent down and kissed the bulging front of my shorts. "Thank you my dirty old man's gorgeous cock."

Angie gave me a long kiss and massaged my cock through the shorts. They both stood up and went to leave.

I gestured at the prominent bulge in my shorts. "Hey, you can't leave me like this?"

They turned round and looked at me.

Simone asked, "If we help you out, do you promise to be very good to us later."

"Oh very, very good."

She looked at Angie, "Then I suppose we could help, what do you think?"

"Well he has been very good so far, so we could be kind." Then they both laughed and came and knelt in front of me.

Simone undid the front of my shorts. Little Andy sprang up in all his glory, grateful to be released from his prison. She gave him a quick kiss. Then she crawled up onto the couch and knelt beside me. Angie pulled my shorts off and got comfortable between my legs.

Angie started by gently sucking my balls and licking my shaft. Simone took my glans in her mouth and ran her tongue all round it. My cock twitched and grew with the attention it was getting. I gave a little groan in appreciation.

The girls got a lot more enthusiastic. Simone was trying to swallow all of my eight inches. Angie had both of my balls in her mouth. The sensations were surging down my shaft and spreading over my groin.

I couldn't help myself. I let my hand move up Simone's leg under her skirt until it found her panty covered ass. My finger slipped under the elastic and sought out the puckered rosebud of her ass hole. I sent it strumming over the delicate opening of her asshole, sending little shivers through her.

As I ran my finger gently round it she wiggled her butt in encouragement. I used the kitty juice that was oozing from her pussy to lubricate my finger. I eased the finger past the tight muscular ring of her ass. Simone froze for a moment. I could feel her trying to relax, and then as she did, she resumed her sucking. My finger slid all the way in and I began finger fucking her ass. Simone arched her back and cried out.

Angie looked up to see what we were doing. "Oh you naughty boy, couldn't you wait?"

I grinned at her, "It's your fault, and it got me thinking about lewd sexual acts I could do with the two of you."

I pushed a second finger in and carried on finger fucking her ass. Simone was panting and had completely forgotten she was sucking me off. Her head was bent over my cock. But her eyes were squeezed shut and her mouth open as she moaned in pleasure.

Angie smiled at my predicament. She moved Simone's head so she could take over sucking me. I abandoned myself to the delights of her mouth. My fingers were moving in and out of Simone's ass. I found I could just reach her clit with my thumb. Simone reacted almost immediately as her orgasm exploded. I could feel her shaking as she collapsed beside me.

I was getting close when I realized I could no longer feel Angie's mouth. I opened an eye and saw she'd taken her panties off. She was poised over my cock and with a grunt she skewered herself on his full length.

She looked back at me. "Christ, you fill me; I wasn't going to waste any of your wigglers."

And she rode me in a reverse cowgirl to my climax. She shuddered as I filled her warm body cavity with my jism. She lay back on me catching her breath, I wrapped my arms round her and she gently caressed them.

She looked at both of us, "I'm sorry, I took advantage of you to fill my cunt with more sperm." Somehow, she didn't seem to be all that apologetic.

I smiled, "Don't be, they are yours for as long as it takes. Just tell us when you want a top up."

Simone looked at me, "Every time you touch me you bring me to new levels of fucking pleasure. I have never had an anal orgasm before."

Angie said, "That wasn't a real anal orgasm. Just wait until he's got his cock in there, then you will know what a proper one is."

"Fuck, it can get better than that?"

Angie laughed. "Oh god yes, it can be amazing, and you haven't lived until you have two cocks inside you at the same time.

She looked at me, "Pete and Andy at the same time. I still have fantasies about that night."

I grinned at the memory

Simone was rocking on the edge of the seat. "Please, please, can we try that?" She asked me. "I want you in my ass and Pete in my kitty."

"Tonight, I promise we will do whatever you want."

Angie stood up and retrieved her panties from the floor. "Wait a moment I have something that will help later."

She disappeared and returned a couple of minutes later. In her hand was an exquisite silver and gold inlayed butt plug.

"I want you to have this," she told Simone.

Simone looked at it in wonder, "I can't, and it's too beautiful for you to give it away."

Angie shook her head, "It's yours now, and I have its bigger brother. They were a gift to me from Pete. I just asked him now and he wants you to have it."

Simone looked from me to Angie with moist eyes. "Thank you, I love you both so much."

Then she asked Angie, "What do I do with it?"

Angie grinned, "Let me show you. You are going to need some lube and I have some. First you coat it in lube."

She showed Simone what she meant. Then she bent Simone over and pulled her panties down and squirted a generous amount on her ass.

"Then you work some around and in your anus." And she matched her words with her actions as her fingers danced around Simone's rosebud.

"Then you slide it in. Don't worry the shape and the collar hold it in place," and she firmly slid it into place.

"Fuucck, that feels big... And you have a bigger one?"

"I do, yours is an inch in diameter. The one I use is an inch and a half."

Simone looked shocked, and then went to remove it.

"No," and Angie pushed her hand away. "You need to leave it in until Andy fucks your ass tonight."

"Christ that's hours away. Do I really need to keep it in?"

"Yes. It really will help"

Simone gingerly pulled her panties up and wriggled her butt trying to find a comfortable position.

Angie told her, "I'd take them off, it's more comfortable that way."

She removed them and walked across the cabin to the kitchen. By the time she got back to me her legs were shaking and I had to hold her up.

She told me, "That is an amazing feeling, pain and pleasure at the same time."

Angie agreed, "It take a bit of getting used to. But after a while it becomes a mild sensation of constant pleasure." And she bent over and flashed her ass. There in all its glory was its bigger brother.

Angie looked at us, "I slipped it in when I went to get yours."

She said hopefully, "I was hoping that after Simone's introduction, you and Pete will fuck me? I want Pete in my ass and you where you should be leaving your cum in order to get me pregnant."

She paused then said wistfully, "I still would like to have you fuck my ass. But it can wait until I'm pregnant."

I smiled at the thought. But the pleasant picture I was building in my mind was interrupted by Pete's call.

"I've got St Raphael in sight, can you come up."

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St Raphael

Angie and I bounced up the cabin stairs to the wheelhouse. Simone followed a bit more gingerly.

Pete watched her with a smile."I take it that you are enjoying your present."

"I am," and she flashed her ass at him and the jewelled butt plug was obvious. "This is very generous of you. I feel guilty, I know that it was a present to Angie, and I'm breaking up a set."